IGCSE Chemistry Organic Workbook 2023 Abul Fazal +92 321 282 5395 Contents Intro to Organic WS 1 5 Alkanes WS 1 18 Alkenes WS 1 21 Alcohols WS 1 25 Acids and Esters WS 1 35 Fuels and Cracking WS 1 49 Organic Chemistry WS 2 58 abul fazal abul fazal 3 Homework Date Particulars abul fazal 4 Homework Date Particulars abul fazal Which pair of metals produces the highest voltage? B 40 removes carbon 200 dioxide from V2Othe 5 32 Which process atmosphere? A C copper 400 and magnesium 2 Fe A combustion of fossil fuels B D magnesium 400 and platinum 2 V2O5 5 B decomposition of carbonates C magnesium and zinc C photosynthesis silver and chips platinum 34 D Some marble (calcium carbonate) are heated strongly and substances X and Y are formed. D respiration 1 2017 JUN P23 Q11 Substance X is a white solid that reacts with water, giving out heat. Substance Y is a colourless 11 gas. Heat energy is produced when hydrocarbons burn in air. 33 Which row shows the conditions used in the manufacture of sulfuric acid by the Contact process? Whichare equations represent What substances X andthis Y?statement? Intro to Organic WS 1 temperature pressure → 2CO2 + catalyst 3H2O 1 /C 2H5OH + 3O/2atm °C X Y 2 C2H4 + 3O2 → 2CO2 + 2H2O 40 chloride 200 calcium oxygen Fe CO2 + 2H2O V O 3 CH 4 + 2O2 →200 40 hydroxide 2 5 calcium carbon dioxide AA BB AC 3 B 1 and 22carbon only dioxide C Fe 1 and 3 only C 1, 2 and 400 calcium oxide DD 400 sulfate calcium 2 D 2 and 3 only oxygenV2O5 2 2017 NOV P21 Q35 34 The Some marble chips (calcium carbonate) are heated strongly and substances X and Y are formed. 35 structures of some organic molecules are shown. Substance X is a white solid that with water, giving a colourless © UCLES 2017 1 over 2 reacts0620/23/M/J/17 3 out heat. Substance Y 4 is[Turn gas. CH3 H H H What are substances X and Y? C H C C H C X Y CH3 H3C H CH3 A calcium chloride oxygen CH3 H H C C H H CH3 H H H C C H H CH3 Which represent an alkane four carbon atoms? B structures calcium hydroxide carbonwith dioxide A C 1 onlycalcium oxide B 2 and 3carbon dioxide C 2 and 4 D calcium sulfate D 3 and 4 oxygen 3 2017 NOV P22 Q35 35 The structures of four organic compounds are shown. S H T U abul fazal H H H H C C C C H H H H H © UCLES 2017 H H H C C H H H H H H C C H C C H H 0620/21/O/N/17 V H H H C C H H H Which compounds are unsaturated? A S only © UCLES 2017 Abul Fazal B T and U C U only 0620/22/O/N/17 D V only [Turn over Intro to Organic WS 1 A calcium chloride oxygen B calcium hydroxide carbon dioxide C calcium oxide D calcium sulfate fractions refinery gas carbon dioxide 6 gasoline oxygen 4 2017 NOV P23 Q35 X 35 The structure of compound R is shown. H H H H kerosene C C C OH diesel oil H H H lubricating fraction petroleum What is R? bitumen A propane B A propanoic alcohol acid C B propanol fuel oil 14 D propene 35 The C diagram naphtha shows the separation of petroleum into fractions. D paraffin 36 Fuel oil and naphtha are two fractions obtained from petroleum. 5 2016 MAR P22 Q36 gasoline 36 What Whichare compounds alkanes? the major are uses of these fractions? compound fuel oil A Wnaphtha formula jet fuel C4H10 chemicals C5H10 making roads A B W and X jet fuel B W and making Z C X and Y petroleum C ship fuel making chemicals D ship fuel YX Z C6H12 Y C6H14 X D Y and Z Z making roads15 6 2016 MAR P22 Q36 bitumen 36 Which of the compounds shown are in the same homologous series? What could X, Y and Z represent? 1 CH3OH 2 CHX3CH2OH Y Z lubricating fraction paraffin abul fazal A 3 diesel CH3COOH oil B 4 CH3CH 2CH2OH lubricating fraction A C 1, 2 and paraffin 3 B © UCLES 2017 D diesel oil paraffin fraction oil 2, 3 and 4 1, 2 lubricating and 4 C0620/23/O/N/17 1, 3 and 4diesel D paraffin diesel oil lubricating fraction 7 2016 JUN P22 Q36 37 Which compounds contain the same number of carbon, hydrogen and oxygen atoms? 36 Which compound is not an alkane, CnH2n+2? W X Y Z A CH3CH2CH2CH3 ethyl methanoate methyl ethanoate methyl methanoate ethyl ethanoate B (CH ) CHCH © UCLES 2016 3 2 0620/22/F/M/16 3 A W and X B W and Y C X and Z D Y and Z C CH3CHCHCH3 D (CH3)3CH 38 What is an advantage of producing ethanol by fermentation of sugar compared to the catalytic addition of steam to ethene? 37 An ester is formed when a carboxylic acid reacts with an alcohol. A The alcohol produced is purer. Which ester is formed when propanoic acid and ethanol react? B The process is faster. A C CH The3CO process uses 2CH2CH 3 high temperature. B D CH The3CO process uses renewable raw materials. 2CH2CH 2CH 3 C Organic CH3CH 2CO Intro to WS 12CH3 D CH3CH2CO2CH2CH3 Abul Fazal 7 15 8 2016 JUN P23 Q36 36 Which compound does not belong to the same homologous series as the other three compounds? CH3OH A B C2H5COOH C C2H5OH D C7H15OH 37 The structure of an alkene and the structure of14an ester are shown. 9 2016 NOV P23 Q36 36 Butane reacts as shown. P H H Q H H catalyst butane and heat C C H H H O butene + hydrogen H C C H C C C 14 What is this type of reaction? O H H H H 35 A Which reaction of ethene is not an addition reaction? combustion H H C C H H H A cracking reaction with bromine B What are the names of P and Q? B polymerisation reaction with hydrogen C P oxygen reaction with reduction C D Q but-1-ene ethyl propanoate D A reaction with steam 37 2017 Substance hasQ36 the following characteristics. B MARZ but-1-ene propyl ethanoate P22 10 36 Ethanol is fuel usedininancars. It can be made from C ethyl propanoate 1 abut-2-ene It burns excess of oxygen to14 form petroleum. carbon dioxide and water. D propyl ethanoate 35 Which fraction ofoxidised petroleum matched to its correctofuse? 2 but-2-ene It is by is airnot to form a liquid smelling vinegar. cracking C 4H10 → C2H4 + C2H6 3 It reacts with carboxylic to form esters. Hacids producing ethanol C2H4 + use 2O → C2H5OH fraction 38 What is an advantage of producing ethanol by fermentation of sugar compared to the catalytic What is substance C2H5OH + 3O burning 2 → 2CO2 + 3H2O addition of steam toZ? ethene? A bitumen making roads A ethane A alcohol produced purer. Compounds of how many is homologous series appear in these equations? B The gasoline fuel for cars B C The ethanoickerosene acidis faster. fuel for ships B A 1 process B 2 C 3 C ethanol naphtha chemical industry C D The process uses high temperature. D 4 abul fazal D ethylis ethanoate 37 2017 Ethanol produced either ethene or sugar. The process usesfrom renewable raw materials. JUN P21 Q36 11 D 36 The diagram shows the structures of two organic molecules. Which type of chemical reaction is used in each case? 38 Ethanol is manufactured by the catalytic addition of steam to ethene and by fermentation. H ethene ethanol sugar → ethanol of using the catalytic addition of steam to Which row shows→an advantage and a disadvantage H H H H O H ethene compared to fermentation? A addition fermentation H C C O H H C C C C H B addition fractional distillation advantage disadvantage H H fermentation the product isH impure H H distillation fast C A H D statement distillation fractional distillation B fast these molecules uses non-renewable materials Which about is not correct? product is pure slow A C They arethe both alcohols. 38 The structural renewable formula of materials an organic compound is shown. slowthey burn in oxygen. B D Theyuses both produce carbon dioxide and water when C CH3CH2COOCH3 They contain different functional groups. What is the name this compound? D They have theofsame general formula. © UCLES 2016 [Turn over 0620/23/M/J/16 A butanoic acid 37 The diagram shows part of the molecule of a polymer. B ethyl ethanoate C methyl propanoate H Abul Fazal D propyl methanoate C H H H H H H H H C C C C C C C C H H H 0620/23/O/N/16 H H H H H H © UCLES 2016 Intro to Organic WS 1 X pH 7.0 Y pH 5.5 13 8 35 Fuel oil, gasoline, kerosene and naphtha are four fractions obtained from the fractional distillation Lime is used to neutralise the soil in one part13 of the garden. of petroleum. 12 2017 JUN P22 Q36 To which part of the garden should added and why? isstatement the order of the boiling pointsthe of lime these fractions? 36 What Which about homologous series isbe not correct? A H2n+2. Alkenes the same formula, Cpoint part have of the garden because lime highest boiling point general → lowest boiling nis B A Each member of the homologous of alkanes differs from the next by CH2. fuel oil →Xkerosene → gasolineseries → naphtha acidic C B Thefuel members of a homologous series all have similar chemical properties. oil →Xkerosene → naphtha → gasoline basic D C Thegasoline members a homologous series have →ofnaphtha → kerosene →allfuel oil the same functional group. Y acidic D naphtha → → fuel Y gasoline → kerosene basic 12 oil 37 The diagram shows part of the molecule of a polymer. 13 2017 JUN P23 Q36 34 Limestone is an important material with many uses. 36 Butane and1methylpropane with Hisomers H molecular H H formula H H C4HH10. 35 Statement Hydrogen H is are used asHa fuel. Limestone is heated to produce ......1...... and carbon dioxide. Which statements arehydrogen correct? C Cburns C in C C to form C water, C CheatCenergy is produced. Statement 2 When the air This reaction is called ......2...... . They have similar properties. H Hchemical H H H H H H H Which is1correct? Which words correctly complete gaps 1 and 2? 2 They have the same general formula. A Both statements andfrom statement 2 explains 1. Which diagram showsare thecorrect monomer which this polymerstatement could be manufactured? 3 They 1 have the same structural formula. 2 B Both not explain statement 1. A statements are correct B but statement 2 does C D A 1, 2 and 3 B 1 and 2 only C 1 and 3 only D 2 and 3 only neutralisation C A Statement 1 lime is correct but 2 is incorrect. H H statement H H H H H lime thermal decomposition D BHStatement H but C H 1 is incorrect. H C C O H C H 2 is correct C statement C C 37 The diagram shows part of the molecule of a polymer. C slaked lime neutralisation 14 2018 MAR P22 Q36 H H H H H H H H H inthermal Hthe same H decomposition Hhomologous H H series? H H 36 Which row identifies compounds D slaked lime 13 C C C C C C C C C functional 38 Ethanol ischemical manufactured by fermentation or by the catalytic addition of steam to ethene. 35 What is not the correct use group of the fraction named? properties 34 Which equation represents theHformation H Hof lime? Hby fermentation H H H instead H What is an advantage of H ethanol manufacture of by the catalytic addition A different different of steam to ethene? name of fraction use A CaCO CaO +theCO 3 → shows 2 Which diagram monomer from which this polymer could be manufactured? B different same A Ethanol manufactured by fermentation is waxes purified by distillation. making B A CaO + H2fuel O →oilCa(OH)2 A B C D C Ethanolsimilar different B manufacture by fermentation produces purer ethanol. B gas oil fuel in diesel engines C Ca H+ 2H2O → Ca(OH)H H2 2 + H H H H H D similar same C Ethanol manufacture by fermentation uses large areas of land. C kerosene jet fuel D Ca(OH)2 + CO2 → CaCO3 + H2O H C H H C C H H C C O H C C D D Ethanol manufacture renewable resources. naphtha by fermentation makinguses chemicals H H H H H H H 35 2018 WhichJUN equation a reaction of methane is correct? P23 representing Q36 15 39 Methane, The formula of anand ester is CH3CH 2CH2COOCH 2CH 3. 36 ethane propane belong to a family of2CH hydrocarbons called alkanes. A CH4 + Cl 2 → CH 3Cl + HCl abul fazal Whichisacid and alcohol react together to make the ester? What + general Cl 2 → formula CH4Cl 2 of an alkane? B CH4the © UCLES 2018 A C 0620/22/F/M/18 C Cn2H2n+1 CH CH2Cl + H2 alcoholC nH42n+ Clacid 2 → B CnH2n–1 D CnH2n+2 [Turn over D A 2CH4 butanoic + 2Cl 2 acid → 2CH3Cl + butanol Cl 2 + H2 37 Which substances can be obtained by cracking hydrocarbons? P23 Q36 16 2018 B NOV butanoic acid propanol 36 A Which two compounds which both contain a double bond? and ethene C ethanol propanoic acidare molecules butanol B and ethanoic hydrogen A D ethanol ethane and propanoic acid acid © UCLES C ethene B 2017 ethane and hydrogen ethanol D C propanol 0620/23/M/J/17 [Turn over 0620/22/M/J/17 [Turn over ethene and poly(ethene) ethanoic acid © UCLES D 2017 ethene and ethanol 37 Ethanol can be formed by: Intro to Organic1 WSfermentation 1 2 reaction between steam and ethene. Abul Fazal 31 Which catalyst is used in the Contact process? A calcium oxide B iron C manganese(II) oxide 9 13 NOV P23VQ37 17 2017 D vanadium( ) oxide 37 X, Y and Z are three hydrocarbons. 32 A white solid Z reacts acid X CH Y hydrochloric CH3–CH=CH Z a gas. CH3–CH2–CH=CH2 2=CH2 with dilute 2 to produce The same gas is produced when compound Z is heated strongly. What do compounds X, Y and Z have in common? What is Z? 1 They are all alkenes. A 2 They are all part of the same homologous series. calcium B 3 carbonate They all have the same boiling point. calcium C A calcium 1, 2 and hydroxide 3 B 1 and 2 only C 1 and 3 only D 2 and 3 only D calcium oxide 38 The diagram shows a reaction sequence. 18 2021 JUN P21 Q33 33 What is the structure X of butanoic acid? butane ethene A CH3CH2CO2H Y Z ethanol carbon dioxide and water B CHrow 3CH2CH2CO2H Which names the processes X, Y and Z? CH3CH2CH2CH2CO2H X Y D CH3CH2CH2CO2CH3 A cracking fermentation C B cracking Z respiration hydration 19 2021 NOV P21 Q33 combustion 11 C distillation fermentation respiration 33 An alkane molecule of molecular formula C8H18 undergoes cracking. The equation for the reaction isdistillation shown. D hydration combustion C8H18 → Q + 2R 39 The structure of an ester is shown. Substance R has two carbon atoms per molecule and decolourises aqueous bromine. What is substance Q? H H C C H H O abul fazal A butane B butene H © UCLES C 2021 ethane H H H H C C C C H H 0620/21/M/J/21 H H C O H [Turn over D ethene Which combination of carboxylic acid and alcohol produces this ester? carboxylic acid alcohol 34 Fuel X produces carbon dioxide and water when it is burned in air. So does fuel Y. A butanoic acid What could X and Y be? B butanoic acid X Y C ethanoic acid A D C H2 propanoic acid B C C8H18 C CH4 H2 D CH4 C8H18 © UCLES 2017 ethanol propanol butanol butanol 0620/23/O/N/17 [Turn over 35 Which molecule contains only single covalent bonds? A propane Abul Fazal B propanoic acid C propene Intro to Organic WS 1 33 What is the structure of the ester formed from ethanoic acid and propanol? B sodium chloride C sodium hydroxide D sulfuric acid A H H H C C B 10 O H C H H 20 2021 NOV P23 Q33 C C H 33 What is theHstructure ofOpropanol? H H A H H C H H O C C C H H O HH C H H C H H O H H H H H H C H C H O H O H O C C H H C O H O H H H C O H C H D O H HH CC C H C H HC C C O HB H C H H H C H H C H D H C C H H H H C C H H O H H H 21 2021 NOV P22 Q34 34 Fuel X produces carbon dioxide and water when it is burned in air. So does fuel Y. © UCLES 2021 0620/23/O/N/21 What could X and Y be? X Y A C H2 B C C8H18 C CH4 H2 D CH4 C8H18 abul fazal © UCLES 2021 Intro to Organic WS 1 0620/22/O/N/21 [Turn over Abul Fazal 11 13 22 2020 NOV P21 Q35 35 The structures of four organic molecules are shown. 1 H 2 H H H C C C H H C H H H C H H H H H H H C C C C H C H H H H H H H 3 4 H H H H H C C C H H C C H H H H H H H H H C H H C C C H H C H H H H Which molecules are structural isomers of structure 1? 12 A 2 and 4 B 2 only C 3 and 4 D 34 Compound Z contains carbon, hydrogen and oxygen. 3 only 36 Which chemical equation for the substitution of12 anatoms alkaneand withtwo chlorine is correct? Molecules of compound Z have four hydrogen carbon atoms. 23 2020 NOV P22 Q35 abul fazal Clcan beCmade +molecule HCl C3Hstructure 8 + Z 2 represents 3H7Cl aby 35 A Which of ethanol? Compound oxidation of an alcohol. C H Cl 2 B C H + Cl C D B H C3H8 + Cl 2 C3H6Cl 2 + H2 H H H H ethene C3H6 + Cl 2 C3H5Cl + HCl ethanol C C H C C C ethanoic H acid H D methyl methanoate 2 What 3isA6compound Z?3 6 A H B C H H H H C C H H D H O H H C O C H O H 36 2021 WhichJUN structures are structural isomers of each other? P21 Q35 24 35 Which statement about homologous series and isomerism is correct? 2 1 A Butane and butene H are H structural H H isomers. B CompoundsHin the C same C homologous C C H series have H theCsame C general C Hformula. C Compounds in the same homologous series have the same molecular formula. H H H H H H H C H Structural isomers have different molecular formulae. D © UCLES 2020 H H 0620/21/O/N/20 36 Which statement about alkanes is correct? 3 A They burn in oxygen. H H H H Abul Fazal B They contain carbon, hydrogen and oxygen atoms. H C C C H H C C They contain double bonds. H [Turn over H 4 H H C C Intro to Organic WS 1 H A Ethanol can be made by fermentation. B Ethanol is oxidised to make ethanoic acid. C Ethanol reacts with oxygen exothermically, 1212making it a good fuel. D Ethanol reacts with propanoic acid to make propyl ethanoate. 34 Ethanol is reacted with acidified potassium manganate(VII). 25 2021 JUN P22 Q35 Which row describes the type of reaction and the type of organic compound formed? 35 Which pair of formulae represents two alkanes? A of8H reaction and C CH4 type 18 organic compound C5H8 BA C2H6 and oxidation carboxylic acid oxidation C5H12 CB C3H6 and alkene dehydration C4H8 DC C10H8 and carboxylic acid D dehydration alkene 36 Which statement about alkanes is correct? 2021 JUN P23 Q35 26 11 35 diagrams show the compounds. A alkane They burn in oxygen. 33 The An molecule of structural molecularformulae formulaofCfour 8H18 undergoes cracking. The equation for the reaction is shown. B They contain carbon, 1 hydrogen and oxygen atoms. 2 C They contain H H bonds. H H C8H18 → Q + 2R H double H H H Substance R has atoms D TheyHcontain ionic bonds. C C Cper Hmolecule andHdecolourises C H C two C carbon C C aqueous C C bromine. What is substance H H H H H Q? 37 Which statements about ethanoic acid are correct? A butane B 1 butene It is a strong acid. C 2 ethane It reacts with ethanol to form an ester. D 3 ethene 3 It has the formula CH3COOH. H H H H C H H H 4 H H H H H H H H H A 1 and 2 only B 1 and 3 only C 2 and 3 only D 1, 2 and 3 34 Fuel X produces carbon dioxide and water when it is burned in air. C does C fuelCY. H H C C C C H H C C So What could X andHY be? H X A C C Y H H2 H H H H H H H C H H H abul fazal Which are structural isomers? B twoCcompounds C8H18 A C 1 andCH 34 D CH4 H2 1 and 4 B C 2 and 3 D 2 and 4 C8H18 36 Which statement about alkanes is correct? 2021 NOV P21 Q35 27 35 A Which molecule They burn incontains oxygen.only single covalent bonds? A B propane They contain carbon, hydrogen and oxygen atoms. B C propanoic aciddouble bonds. They contain C propene D propyl propanoate D 2021 They contain ionic bonds. © UCLES 0620/22/M/J/21 [Turn over 36 Alkanes react with chlorine to form chloroalkanes. Which statement about the reactions of alkanes with chlorine is correct? © UCLES 2021 0620/23/M/J/21 A Alkanes react with chlorine by addition. B The gaseous product turns red litmus blue. C The chlorine atom in chloroethane is covalently bonded. Intro to WS 1 formula of the chloroalkanes is CnH2nCl. D Organic The general Abul Fazal 13 12 28 2021 NOV P22 Q35 35 The structures of four organic molecules are shown. H H C O Cl H C O H H H H H C C H H H O O H H C H H How many different homologous series are represented by these molecules? A 1 B 2 C 36 Which statement about ethene is correct? 29 2019 JUN P21 Q36 3 D 4 14 36 A WhyItishas ethanol a member of theChomologous series of alcohols but propane is not? the chemical formula 2H6. B A It burns in excess oxygenatoms producing carbon dioxide and water. Ethanol has two carbon per molecule but propane has three. C B to produce an orange solution. is obtained from petroleum. It reacts can withbe Br2made Ethanol from ethene but propane D C It reacts is with oxygen form ethanol. Ethanol a liquid buttopropane is a gas. D Ethanol contains the same functional group as other alcohols but propane does not. 37 Ethanol is manufactured by fermentation of sugars or by catalytic hydration of ethene. 15 37 Chlorine reacts with methane. WhichJUN row states an advantage of each method? P22 Q36 30 2019 36 Which Which statements statement about homologous series is not correct? are correct? fermentation hydration A All homologous series are hydrocarbons. 1 produces The reaction place in the dark. A purertakes ethanol is a batch process B Members of a homologous series have the same functional group. 2 produces The reaction chlorine with methane forms chloromethane. B purerof ethanol is a continuous process C Members of a homologous series have similar chemical properties. 3usesChloromethane reacts with chlorineisto produce dichloromethane. C a renewable resource a batch process D The alkanes are an example of a homologous series. 4usesThe reaction ofresource chlorine with methane is an addition reaction. D a renewable is a continuous process abul fazal A 1 and 2 B 1 and 3 C 13 2 and 3 D 3 and 4 37 In bright sunlight, ethane and chlorine combine in substitution reactions. P23 Q36 31 38 2019 WhichJUN statements about unsaturated hydrocarbons are correct? 36 Which about homologous series are correct? Which statements compound is not formed in these reactions? 38 Which statements ethanoic acid are correct? 1 They about containaqueous both single and double bonds. B Chave C C2Hproperties. D HCl A C2H31Cl All members 2H5Clsimilar chemical 4Cl 2 2 turnacid aqueous bromine from colourless to brown. 1 They Ethanoic contains the functional group –COOH. 2 All members have the same molecular mass. 3 can acid be manufactured by cracking. 2 They Ethanoic reacts with carbonates to produce hydrogen. 38 What are the properties of aqueous ethanoic acid? 3 Ethane and ethene are members of the same homologous series. 3 2 only Ethanoic turns Universal A 1 and B acid 1 and 3 only C Indicator 2 and 3paper only blue. D 1, 2 and 3 4 Ethane and propane arereacts members of the same homologous series. with 4 decolourises Ethanoic acid has a pH lower than pH 7. turns damp red calcium carbonate to bromine water blue4 A 1 and 3 B 1 and 4make carbon C 2dioxide and 3 Dlitmus 2 and A 1 and 2 B 1 and 3 C 1 and 4 D 2 and 4 A 37 Which type of reaction takes place when methane reacts with chlorine in the presence of 39 The of an B structure ester is shown. ultraviolet light? A C addition B D cracking © UCLES 2021 CH3 O C 0620/22/O/N/21 C polymerisation OCH2CH2CH3 39 The structures of four molecules are shown. D substitution What is the name of the ester? 2 3 1 Abul Fazal A ethyl propanoate 38 Which statement about aqueous ethanoic acid H H is correct? H H O B methyl propanoate A H It reacts with metal H carbonates H salts, C C OH to form C hydrogen C C and OH water. H 4 H H C C Intro to Organic WS 1 O C A non-renewable manganese(IV) oxide B renewable C vanadium(V) oxide C non-renewable D nickel D renewable B high slow low slow low 14 high fast fast 2020 JUN P21 Q36 32 35 Ethanol is made on an industrial scale by the fermentation of sugars or by the reaction of ethene 36 with Which statement about homologous series is correct? steam in the presence of a suitable catalyst. A Members of a homologous series have theethene same structural What is a disadvantage of making ethanol from rather thanformula. by fermentation? B A of aproduction homologous series all have similar chemical properties. AMembers continuous process is used. C B of a homologous all have similar physical properties. AMembers non-renewable raw materialseries is used. D C Members ofisallvery homologous series are hydrocarbons. The product pure. D The rate of reaction is very high. 33 2020 JUN P22 Q36 36 Which statement about compounds in the same homologous series is correct? A They have the same chemical properties because they have the same number of carbon atoms. B They have the same physical properties because they have the same number of carbon atoms. C They have different chemical properties because they have different numbers of carbon atoms. 0620/21/M/J/20 have different physical properties because they have different numbers of [Turn carbonover atoms. © UCLES D 2020 They 13 34 2020 JUN P23 Q36 36 Which statement about a homologous series is correct? A All members have the same general formula. B All members have the same molecular formula. C All members have similar physical properties. D Members show a trend in their chemical properties. © UCLES 2020 0620/22/M/J/20 [Turn over abul fazal 37 Increasing the number of atoms in one molecule of a hydrocarbon increases the amount of energy released when it burns. What is the correct order? more energy released less energy released A ethene ethane methane B ethene methane ethane C methane ethane ethene D methane ethene ethane 38 A small quantity of a solid chemical is added to a large excess of aqueous ethanoic acid. No bubbles of gas are seen and the solid dissolves to give a colourless solution. What was the solid chemical? A calcium hydroxide B copper(II) oxide Intro to Organic WS 1 C magnesium D sodium carbonate Abul Fazal H H H C C H H H H H C C 15 H H H H H C C H H H O H H C O C O H H 35 2020 NOV P22 Q36 36 Which structures are structural isomers of each other? 2 1 H H H H H C C C C H 13 H H H H C C C H H H H H H H H So C does H fuel Y. 34 Fuel X produces carbon dioxide and water when it is burned in air. H What could X and Y be? X Y 3 A C HH H H 36 The fractional distillation2of petroleum is shown. B C HC8HC18 C C H C CH4 D CH4 HH 2 H C8H18 C 4 13 H H H H H H hydrogen 1, 2 and 4 only B C 1carbon and 3 monoxide only H H C C C refinery gas C H H H H gasoline fraction 35 A What main 1, is 2,the 3 and 4 constituent of natural gas? A B H paraffin fraction diesel oil D C 2methane and 4 only lubricating fraction petroleum D nitrogen 37 Which molecule is not produced by an addition reaction of ethene? 36 2021 NOV P23 Q36 CHstatement B CH2BrCH C of CH D CH3CH2CH3 36 A Which describes the members a homologous series? 3CH3 2Br 3CH2OH bitumen abul fazal A compounds withleast the volatile? same physical properties Which fraction is the B A compounds containing the same functional group bitumen C B compounds containing the same number and type of bonds diesel oil D C compounds obtained from the same raw material gasoline fraction D refinery gas 37 2019 The structures two compounds are shown. MAR P22ofQ37 37 37 Which statement about of a homologous series is correct? H members H H H O 0620/22/O/N/20 © UCLES 2020 A B C Successive members differ by CH3. H C C O C H C C Successive members have a molecular mass that differs by 14. H H H H H They have the same molecular formula. O C O H Which statements about these compounds D They have identical physical properties. are correct? 1 They have the same molecular formula. 38 Ethanol is manufactured on a large scale by fermentation. 2 They have similar chemical properties. Which statement about is correct? 3 They are fermentation structural isomers. A It is a continuous process. A 1 only B 1 and 2 B A renewable raw material is used. Abul Fazal C It is a very fast reaction. D The ethanol produced is pure. C 2 and 3 D 1 and 3 Intro to Organic WS 1 A Bitumen is used as a fuel for ships. B Coal, natural gas and oxygen are all fuels. C 16 Hydrogen is the main constituent of natural gas. D Petroleum is separated into useful substances by fractional distillation. 38 2019 NOV P23 Q37 37 Which products are obtained by the cracking of an alkane? alkene hydrogen water 13 36 Which statement about a homologous series A is correct? A B All members have the same general formula. formula. B C All members have the same molecular physical properties. C D All members have similar D Members show a trend in their chemical properties. 39 2020 JUN P23 Q37 37 Increasing the number of atoms in one molecule of a hydrocarbon increases the amount of energy released when it burns. What is the correct order? © UCLES 2019 more energy 0620/23/O/N/19 less energy released released A ethene ethane methane B ethene methane ethane C methane ethane ethene D methane ethene ethane 15a large excess of aqueous ethanoic acid. 38 A small quantity of a solid chemical is added to 40 2021 MAR P22 Q37 37 The formula of of gas a hydrocarbon is C xHsolid y. No bubbles are seen and the dissolves to give a colourless solution. The its chemical? complete combustion is shown. Whatequation was thefor solid A abul fazal calcium hydroxide CxHy + 8O2 5CO2 + 6H2O ) oxide of x and y? B copper( What are theIIvalues C magnesium x y D sodium carbonate A 5 6 B 5 12 39 Alkanes undergo substitution reactions with chlorine in the presence of ultraviolet light. C 6 5 Which equation shows a reaction of this type? D 12 5 A C3H6 + Cl 2 → C3H6Cl 2 B C3H8 + Cl 2 → C3H6Cl 2 + H2 132CH2CH3. 38 The formula of an ester is CH3CH2CH2COOCH C C3H8 + 2Cl 2 → C3H6Cl 2 + 2HCl 37 Which How much is needed to reacttocompletely with 0.02 moles of butene to make butane? acid hydrogen and alcohol react together make the ester? D C3H6 + 3 Cl 2 → C3H5Cl + HCl B 0.48 dm3 C 0.96 dm3 D 1.20 dm3 A 0.24 dm acid alcohol 41 2021 JUN P23 Q37 A butanoic acid butanol 38 What is an advantage of the fermentation process for producing ethanol compared with the catalytic addition ofacid steam to ethene? B butanoic propanol propanoicrequires acid less heat butanol A C Fermentation energy. © UCLES 2020 0620/23/M/J/20 D Ethanol propanoic acid propanol B Organic from needs to be distilled. Intro to WS 1 fermentation C Raw materials for fermentation are non-renewable. 39 Molecule 1 undergoesprocess a process to make molecule 2. rather than continuously. D The fermentation is carried out in batches [Turn over Abul Fazal A compounds with the same physical properties B compounds containing the same functional group C 17 type of bonds compounds containing the same number and D compounds obtained from the same raw material 42 2021 NOV P23 Q37 37 The structures of two compounds are shown.12 14 H molecules O are shown. 35 The structures of fourHorganic H H O H C ofCatoms O inC one molecule of Ha hydrocarbon C C C increases theHamount of 37 Increasing the number energy released when it burns. H O H H H O H H H H H O What is the correct order? H C Cl H C O H H C C O H Which statements about these compounds are correct? H C H H less energy H H more energy H 1released They have the same molecular formula. released 2 ethene They have similar chemical How different homologous series areproperties. represented A many ethane methane by these molecules? 3 ethene They are isomers. B structural 2 methane C AB 1 A C 1 onlymethane B ethane 1 and 2 C 36 Which about ethene is correct? D statement methane ethene 3 ethane D 2ethene and 3 4 D 1 and 3 ethane A It JUN has the chemical P21 Q38 formula C2H6. 43 2020 38 Some properties of an oxygen organic producing compoundcarbon J are listed. B It burns in excess dioxide and water. orange solution. It reacts 2 to produce ● with It is aBrliquid at rooman temperature. C [Turn over © UCLES D 2021 It reacts oxygen in towater. form ethanol. 0620/23/O/N/21 ● with It is soluble ● A solution of J reacts with calcium carbonate to form carbon dioxide. 37 Ethanol is manufactured by fermentation of sugars or by catalytic hydration of ethene. ● A solution of J has a pH of 3. Which row states an advantage of each method? In which homologous series does J belong? A alkane fermentation hydration B A alkene produces purer ethanol is a batch process C B alcoholproduces purer ethanol is a continuous process uses aacid renewable resource D C carboxylic is a batch process D abul fazal uses a renewable resource is a continuous process 39 2021 Ethane, C2HP22 6, reacts NOV Q38with chlorine in a substitution reaction. 44 38 What Whichare statements about hydrocarbons are correct? the products ofunsaturated this reaction? A 1 Theyand contain both single and double bonds. chloroethane hydrogen B 2 Theyand turnhydrogen aqueous bromine chloroethane chloride from colourless to brown. C 3 Theyand can hydrogen be manufactured by cracking. chloroethene D A chloroethene 1 and 2 only and B hydrogen 1 and 3 chloride only C 2 and 3 only © UCLES 2021 0620/22/O/N/21 Abul Fazal © UCLES 2020 0620/21/M/J/20 D 1, 2 and 3 Intro to Organic WS 1 A CaCO3 → CaO + CO2 13 B CaO + H2O → Ca(OH)2 12 18 35 The structures of four organic molecules are shown. C Ca + 2H2O → Ca(OH)2 + H2 34 Ethanol is reacted with acidified potassium manganate(VII). 1 2 D Ca(OH)2 + CO2 → CaCO3 + H2O Which row describes organic formed? H theH type H of reaction and the type of H H compound H H 1 2018 NOV P23 Q35 Alkanes WS 1 35 Which equation of methane is C C Ca reaction H H correct? C C type Hofrepresenting reaction organic compound H HCl A A CH4 + Cl 2 →H CH3Cl + oxidation carboxylic acid H C H B B CH4 + Cl oxidation alkene 2 → CH4Cl 2 H C H acid C C CH4 + dehydration Cl 2 → CH2Cl 2 + Hcarboxylic 2 H H C C C H H H H H H Cl + Cl alkene D D 2CH4 +dehydration 2Cl 2 → 2CH 3 2 + H2 3 molecules which both 4 bond? 36 Which two compounds a double 35 The diagrams show theare structural formulae of 14 fourcontain compounds. MAR P22 Q34 2 2021 H chlorine. H H H 34 A Propane reacts with ethane and ethanoic 1acid 2 C H C C H H C H B ethane and Which row shows aHcondition for this reaction and H Hrequired H H ethanol H identifies theHtypeHof reaction? H H H acid C ethene and ethanoic H H HC condition HH C CC H CH C C C H H type of reaction C CC C C C H C D ethene and ethanol H H H H H HHacidHcatalyst A phosphoric addition H H H H H H C H B phosphoric acid substitution H C H 37 Ethanol can be formed by:catalyst H H C ultraviolet light addition 1 fermentation D molecules ultraviolet light isomers of structure substitution Which are structural 1? 2 reaction between steam and ethene. 3 4 A 2 and 4 B 2 only C 3 and 4 D 3 only H aHcatalyst? H H use H H H H H Which of these processes 35 The pie chart represents the composition of natural gas. 3 2020 NOV P21 Q36 Cthe C C C H C C for H H with C chlorine C C is correct? 1 represents 2methane? 36 Which equation substitution of an alkane Whichchemical sector H C3H7 ClH + HCl A AC3H8 + Cl 2 H H C H B BC3H6 + Cl 2 C3H6 Cl 2 H Cl 2 + H2 C CC3H8 + Cl 2 C3H6 A B C H H D H H C H H H abul fazal H DC H structural isomers? Which two compounds are D 3 6 + Cl 2 C3H5Cl + HCl A 1 and 3 B 1 and 4 C 2 and 3 D 2 and 4 4 2021 JUN P23 Q36 36 Which statement about alkanes is correct? A They burn in oxygen. B They contain carbon, hydrogen and oxygen atoms. 36 CWhich statement describes the reaction between ethene and steam? They contain double bonds. A a cracking reaction which produces 0620/23/O/N/18 ethane and hydrogen gas as products B an addition reaction which produces ethanol as the only product C an oxidation reaction which produces ethanoic acid as the only product D 2018 They contain ionic bonds. © UCLES © UCLES 2020 D 0620/21/O/N/20 a slow reaction producing ethanol and carbon dioxide © UCLES 2021 Alkanes WS 1 [Turn over [Turn over 0620/23/M/J/21 Abul Fazal A propane B propanoic acid C propene D propyl propanoate 19 5 2021 NOV P21 Q36 36 Alkanes react with chlorine to form chloroalkanes. 14with chlorine is correct? Which statement about the reactions of alkanes 36 A WhyAlkanes is ethanol a member of theby homologous react with chlorine addition. series of alcohols but propane is not? B A The gaseous product turns red litmus blue. but propane has three. Ethanol has two carbon atoms per molecule C B The chlorine atom in chloroethane covalently Ethanol can be made from ethene is but propane bonded. is obtained from petroleum. D C The general the chloroalkanes Ethanol is a formula liquid butofpropane is a gas. is CnH2nCl. D Ethanol contains the same functional group as other alcohols but propane does not. 6 2019 JUN P21 Q37 37 Chlorine reacts with methane. Which statements are correct? © UCLES 2021 1 [Turn over 0620/21/O/N/21 15 The reaction takes place in the dark. 2 The about reaction of chlorineseries with methane forms chloromethane. 36 Which statement homologous is not correct? A 3 Chloromethane with chlorine to produce dichloromethane. All homologous series arereacts hydrocarbons. B 4 The of chlorine is functional an additiongroup. reaction. Members of areaction homologous serieswith havemethane the same 13 1Members and 2 of a homologous B 1 and 3series have C similar 2 andchemical 3 D 3 and 4 properties. A C 36 Which statements about homologous are correct? D The alkanes are an example of a series homologous series. 38 Which statements about aqueous ethanoic acid are correct? 7 2019 JUN Q37 have similar chemical properties. 1 P22 All members 37 In bright 1sunlight, ethane and chlorine combine in substitution reactions. Ethanoic acid contains the functional 2 All members have the same moleculargroup mass.–COOH. Which compound is not formed in these reactions? 2 Ethane Ethanoic acid reacts with carbonates tosame produce hydrogen.series. 3 and ethene are members of the homologous A Ethanoic acid turns B C C Indicator C2H D HCl C2H4 and propane are members of4Cl the2paper sameblue. homologous series. 33Cl Ethane 2H 5Cl Universal abul fazal 4 3 Ethanoic has4a pH lower pH37. A 1 and B acid 1 and C than 2 and 38 What are the properties of aqueous ethanoic acid? 8 2019 A 1 JUN and 2P23 Q37 B 1 and 3 C 1 and 4 D 2 and 4 D 2 and 4 37 Which type of reaction takes placereacts whenwith methane reacts with chlorine in the presence of decolourises turns damp red ultraviolet light? calcium carbonate to 39 The structure of an ester bromine wateris shown. litmus blue make carbon dioxide A addition O B A cracking CH3 C C B polymerisation OCH2CH2CH3 D C substitution D is the nameof the ester? What 38 Which statement about aqueous ethanoic acid is correct? A ethyl propanoate 39 A The structures of metal four molecules aretoshown. reactspropanoate with carbonates form salts, hydrogen and water. B It methyl 2 3 1 B reacts with metal oxides to form salts and oxygen. C It propyl ethanoate C reacts with reactiveHmetals to form saltsHandHhydrogen. H O methanoate D It propyl D H It turns damp red H litmus C C paper OH blue. H C C C OH OH H 39 Fazal The structure of ester W is shown. Abul H H H Which molecules react together to form the ester propyl methanoate? H O 0620/21/M/J/19 © UCLES 2019 4 H H H C C C H H OH Alkanes WS 1 O A A alkane ethene ethane methane B B alkene ethene C methane C alcohol D methane D carboxylic acid methane ethane ethane ethene 20 ethene ethane 9 2020 JUN P21 Q39 38 Ethane, A small quantity of a solid chemicalinisaadded to a large excess of aqueous ethanoic acid. with chlorine substitution reaction. 39 C2H6, reacts No bubbles gas are seen the solid dissolves to give a colourless solution. What are theofproducts of thisand reaction? Whatchloroethane was the solidand chemical? A hydrogen A B calcium hydroxide chloroethane and hydrogen chloride B C copper(II) oxide chloroethene and hydrogen C D magnesium and hydrogen chloride chloroethene D sodium carbonate 10 2020 JUN P23 Q39 39 Alkanes undergo substitution reactions with chlorine in the presence of ultraviolet light. Which equation shows a reaction of this type? A C3H6 + Cl 2 → C3H6Cl 2 B C3H8 + Cl 2 → C3H6Cl 2 + H2 C C3H8 + 2Cl 2 → C3H6Cl 2 + 2HCl © UCLES 2020 0620/21/M/J/20 © UCLES 2020 0620/23/M/J/20 D C3H6 + Cl 2 → C3H5Cl + HCl [Turn over abul fazal Alkanes WS 1 Abul Fazal A extraction of aluminium food preservative electrolysis B extraction of aluminium water treatment B fractional distillation 21 C manufacture of sulfuric acid food preservative C incomplete combustion 12water treatment D manufacture of sulfuric acid D thermal decomposition 34 Limestone is an important material with many 14 uses. 1 2017 MARisP22 Q35 34 Limestone used in many industrial processes. 35 Which What isreaction notisthe correct the......1...... fraction named? Limestone heated to use produce and carbon dioxide. 35 of ethene isofnot an addition reaction? In which process is it not used? A with This reaction reaction is called ......2...... . name ofbromine fraction use A manufacture of alkenes B A reaction fuelhydrogen oil complete gapsmaking Which words with correctly 1 and waxes 2? B manufacture of cement C B reaction with gasoxygen oil fuel in diesel engines 1 iron 2 C manufacture of D C reaction with steam kerosene jet fuel neutralisation D A manufacturelime of lime D naphtha making chemicals B lime in cars. It can thermal decomposition 36 Ethanol is a fuel used be made from petroleum. A Alkenes WS 1 2 2018 JUN P21 Q36 35 What correct named? C is not the slaked limeuse of the fraction neutralisation 36 Which reaction is not a reaction which undergo? cracking C4Halkenes 10 → C2H4 + C2H6 D slaked lime thermal decomposition name of fraction use A bromination producing ethanol C2H4 + H2O → C2H5OH making waxes B A hydration fuel oil C2H5OH + 3O2 → 2CO2 + 3H2O burning 35 What is not the correct use of the fraction named? gas oil fuel in diesel engines C B hydrogenation Compounds of how many homologous series appear in these equations? name of fraction use kerosene jet fuel D C hydrolysis A 1 B 2 C 3 D 4 D naphtha making A fuel oil makingchemicals waxes 37 Which substances can by cracking B JUN oil be obtainedfuel in diesel hydrocarbons? engines P22gas Q36 3 2018 37 Ethanol is produced from either ethene or sugar. 36 A Which statement about alkenes is not correct? and ethene C ethanol kerosene jet fuel Which type of chemical reaction is used in each case? B and hydrogen naphtha making chemicals A D ethanol They decolourise aqueous bromine. C B ethene andcontain hydrogen Theyethene only the elementssugar carbon and hydrogen. → ethanol → ethanol 36 Methane, andhydrogen propane to belong to a family of hydrocarbons called alkanes. D and poly(ethene) C A ethene They ethane react with formfermentation alkanes. addition What is thereact general ofproduce an fractional alkane? D B They withformula steam to carboxylic acids. addition distillation A C CnH2n distillation B CnH2n+1 C CnH2n–1 D CnH2n+2 fermentation 37 Which substances can be obtained by cracking hydrocarbons? Q37 4 2018 D JUN P23 distillation fractional distillation 37 Which substances can be obtained by cracking hydrocarbons? A ethanol and ethene abul fazal © UCLES 0620/21/M/J/18 B 2018 ethanol and and hydrogen A ethanol ethene 38 The structural formula of an organic compound is shown. C B ethene and hydrogen ethanol [Turn over CH3CH2COOCH3 D ethene ethene and and hydrogen poly(ethene) C What is the name of this compound? D ethene and poly(ethene) A butanoic acid © UCLES B 2018 ethyl ethanoate C methyl propanoate D propyl methanoate © UCLES 2018 0620/22/M/J/18 0620/23/M/J/18 Abul Fazal © UCLES 2017 [Turn over Alkenes WS 1 0620/22/F/M/17 A row shows compound 34 Which the conditions usedcracking for the manufacture of sulfuric acid in the Contact process? 34 Propane reacts with chlorine. B compound fractional distillation pressure Which row shows /aatm conditiontemperature required for/ C this reactioncatalyst and identifies the type of reaction? C mixture cracking 22 A 250 200 vanadium(V) oxide condition type of reaction D mixture fractional distillation B 2 450 vanadium(V) oxide A MAR phosphoric acid catalyst addition 5 2020 P22 Q36 C 250 200 iron 36 Which statements B phosphoricabout acid propene catalyst are correct?substitution D 2 450 iron C ultravioletcontains light only single bonds. addition 1 Propene D ultravioletdecolourises light substitution 2 Propene 35 Which calcium compound does not bromine neutralisewater. an acid soil? 3 Propene is obtained by cracking. A calcium oxide 35 The pie chart represents composition of natural gas. 4 Propene is athe hydrocarbon. B calcium sulfate Which sector represents methane? A calcium 1 and 4 hydroxide B 2, 3 and 4 C 2 and 4 only C D 4 only D calcium carbonate B C D A 37 Which row describes the production of ethanol and its properties? 6 2020 NOV P23 Q36 36 Which product is obtained when bromine reacts with propene, CH3CH=CH2? can be made can be made is used as a is used as a from glucose from ethene fuel solvent A CH CH=CHBr 3 B A CH3CBr=CHBr key 2 C B CH3CH2CHBr = yes 2Br D C CH3CHBrCH 12 = no D structures of four organicmolecules are 35 The shown. 7 2021 MAR P22 Q36 © UCLES 2020 H 0620/23/O/N/20 36 WhichHstatement describesOthe reaction between ethene H and H steam? AH aCcracking Cl reactionH which C produces O H ethane and H hydrogen C C gas O asHproducts B an H addition reaction which produces ethanol as theHonlyHproduct © UCLES 2020 0620/22/F/M/20 C an oxidation reaction which produces ethanoic acid as the only product O H C H H[Turn over Howamany series and are represented by these molecules? D slow different reaction homologous producing ethanol carbon dioxide A 1 abul fazal B 2 C 3 D 4 8 2021 NOV P22 Q36 36 Which statement about ethene is correct? A It has the chemical formula C2H6. B It burns in excess oxygen producing carbon dioxide and water. C It reacts with Br2 to produce an orange solution. D It reacts with oxygen to form ethanol. 37 Ethanol is manufactured by fermentation of sugars or by catalytic hydration of ethene. Which row states an advantage of each method? © UCLES 2021 fermentation 0620/22/F/M/21 hydration A produces purer ethanol is a batch process B produces purer ethanol is a continuous process C uses a renewable resource is a batch process D uses a renewable resource Alkenes WS 1 is a continuous process 38 Which statements about unsaturated hydrocarbons are correct? Abul Fazal H H H H H H H O H 23other? 36 Which structures are structural isomers of each 1 2 14 9 2020 NOV P21 Q37 H H H H H H H 37 Propene is an alkene that reacts with bromine, steam and hydrogen as shown. H C C C C H H C C C H H H H H H H H H C C C H H C H H H bromine 3 H H J H H hydrogen 4 steam H H C C C H What are the products of these reactions? H H J K H C H A H bromopropane dibromopropane 1, 2, 3 and 4 C dibromopropane B 1, 2 and 4 only D bromopropane C 1 and 3 only A B H L H H H C C C H H H L C H K propanol Hbutane propanoic acid propane propanol propane propanoic acid butane H D 2 and 4 only 38 The flow chart shows the preparation of ethanol and some important chemistry of ethanol. 10 2020 NOV P22 Q37 fermentation process Y of ethene? 37 Which molecule an addition reaction substance X is not produced by ethanol carbon dioxide + substance Z A CH3CH3 B What are X, Y and Z? CH2BrCH2Br X C CH3CH2OH 13 Y 11 2021 JUN P21 Q38 combustion 38 P,AQ, R and yeast S are four organic compounds. D CH3CH2CH3 Z oxygen abul fazal glucose hydrocarbon. combustion steam PB is an unsaturated C glucose polymerisation water Q burns but otherwise is unreactive. D yeast fermentation glucose R contains a C–C single bond and a C=C double bond. 39UCLES Which about aqueous ethanoic acid are correct? © 2020statements 0620/22/O/N/20 S undergoes addition polymerisation. 1 It is an are alkane. Which compounds alkenes? A 2 R Itonly reactsBwithP, sodium form carbon P and R andcarbonate S C toP, Q and S dioxide. D Q, R and S 3 It changes the colour of litmus solution from blue to red. 4 It of is a synthetic hydrocarbon. 39 The structure polymer is shown. A BO 1 and 4 1 andO2 C C C O2 and 3 N N H H C O D 3 and 4 O C N N C H H The2020 structure shows that it is a ......1......0620/21/O/N/20 . It is formed by ......2...... polymerisation. © UCLES Which words complete gaps 1 and 2? Abul Fazal 1 2 Alkenes WS 1 B monomer C polymer D saturated 24 12 2021 NOV P21 Q38 38 Propene reacts with steam to form propanol. C3H6(g) + H2O(g) → C3H7OH(g) Which type of reaction takes place? A addition B condensation C oxidation D substitution 14 39 WhichNOV statement about aqueous ethanoic acid is correct? 13 2021 P23 Q38 38 Some reactions of substance Q are shown. A It reacts with magnesium to produce a salt and hydrogen. add steamto produce a salt and hydrogen. It reacts with sodium hydroxide under pressure and salts a catalyst It reacts with ammonium to produce ammonia. add bromine ethanol is made 1,2-dibromoethane Q It turns red litmus blue. is made add hydrogen and a catalyst B C D P What is P? A ethane B ethanoic acid C ethene D poly(ethene) abul fazal 39 Proteins and starch are natural polymers. Which row identifies the method of polymerisation of proteins and starch? © UCLES 2021 0620/21/O/N/21 proteins starch A addition addition B condensation condensation C addition condensation D condensation addition Alkenes WS 1 Abul Fazal 25 Alcohols WS 1 13 1 2016 MAR P22 Q37 37 The statements below are about the alcohol homologous series. The alcohols have the same ......1...... formula. The alcohols have ......2...... chemical properties because they have the same ......3...... . 14 The melting points of the alcohols ......4...... as the number of carbon atoms increases. 36 Butane reacts as shown. Which words correctly complete gaps 1–4? catalyst butane butene + hydrogen and heat 1 2 3 4 A is this type general What of reaction? different functional group decrease general A B combustion similar electronic structure increase B C cracking general similar functional group increase 14 molecular similar functional group increase C D polymerisation 35 Which reaction of ethene is not an addition reaction? D reduction reaction withrepresents bromine a compound that dissolves in water to form an acidic solution? 38 A Which structure 2 2016 NOV P23 Q37 B reaction withthe hydrogen 37 Substance Z has following A characteristics. B C reaction oxygen H ofHoxygen to form carbon dioxide H water. H H and 1 Itwith burns in anHexcess D reaction steam by air to form a liquid smelling of vinegar. 2 Itwith is oxidised H H C C C H C C C 3 It reacts with carboxylic acids to form esters. H H H H H 36 Ethanol is a fuel used in cars. It can be made from petroleum. What is substance Z? cracking C4H10 → C2H4 + C2H6 A ethane C D producing ethanol C2H4 + H2O → C2H5OH B ethanoic acid H H H H H H O C2H5OH + 3O2 → 2CO2 + 3H2O burning C ethanol H C C C H C C C C O H Compounds of how many homologous series appear in these equations? D ethyl ethanoate O H H H H H H H A 1 B 2 C 3 D 4 38 Ethanol is manufactured by the catalytic addition of steam to ethene and by fermentation. abul fazal 3 2017 MAR P22 Q37 37 Which Ethanolrow is produced either ethene or sugar. shows anfrom advantage and a disadvantage of using the catalytic addition of steam to ethene compared to fermentation? Which type of chemical reaction is used in each case? A A B B C C D D advantage disadvantage ethene → ethanol sugar → ethanol fast the product is impure addition fermentation fast uses non-renewable materials addition fractional distillation the product is pure slow distillation fermentation uses renewable materials slow distillation fractional distillation 38 The structural formula of an organic compound is shown. © UCLES Abul Fazal2016 What is the name of this compound? CH0620/22/F/M/16 3CH2COOCH3 [Turn over Alcohols WS 1 D Ca(OH)2 + CO2 → CaCO3 + H2O 35 Which equation representing a reaction of methane is correct? 26 A CH4 + Cl 2 → CH3Cl + HCl 14 4 2018 MAR P22 Q37 CH4Cl 2 B CH 4 + Cl 2 → 37 Three chemical reactions are shown. C CH4 + Cl 2 → CH2Cl 2 + H2 D catalytic addition of steam to ethene 2CH1 4 + 2Cl 2 → 2CH3Cl + Cl 2 + H2 15 2 combustion of ethanol 36 Which Which two molecules both contain a double bond? 3 compounds fermentation of glucose 36 compound doesarenot belong which to the same homologous series as the other three compounds? A which ethane In of and the ethanoic reactionsacid does the relative molecular mass of the carbon-containing compound B C2H5COOH C C2H5OH D C7H15OH A CH3OH decrease? B ethane and ethanol A 1 and 2and ethanoic B 1acid only C 2 and 3 D 3 only C ethene 37 The structure of an alkene and the structure of an ester are shown. D ethene and ethanol P Q 38 How is ethanol produced by fermentation? 5 2018 NOV P23 Q37 H formed H conditions H 37 A Ethanol can be by: H at 30 °C using anaerobic B H1 anaerobic C C conditions C C at H 450 °C using fermentation H C 2 steam reaction using at 30between °C H steam and ethene. H H H C C H H O C O D using steam at 450 °Cuse a catalyst? Which of these processes H H C C H H H What are the1 names of P 2and Q? 39 Which substances react together to form ethyl propanoate? A P Q A ethanoic acid and propanol B BA ethanolbut-1-ene and propene ethyl propanoate C propyl ethanoate B but-1-ene C ethene and propanol D ethyl propanoate C but-2-ene D propanoic acid and ethanol D but-2-ene propyl ethanoate 6 2016 JUN P23 40 The structure of aQ38 chlorofluorocarbon polymer is shown. 38 What is an advantage of producing ethanol by fermentation of sugar compared to the catalytic CH3 Cl CH3 Cl addition of steam to ethene? abul fazal A The alcohol produced is purer. C C C C B The process is faster. H F H F C The process uses high temperature. Which monomer is used to make this polymer? 0620/23/O/N/18 D The process uses renewable raw materials. A B [Turn over © UCLES 2018 © UCLES 2018 Alcohols WS 1 C D CH3 Cl H Cl CH3 F CH3 H C C C C C C C C F H CH3 F Cl H Cl F 0620/22/F/M/18 Abul Fazal A ethane B ethanoic acid C ethanol D ethyl ethanoate 27 7 2016 NOV P23 Q38 38 Ethanol is manufactured by the catalytic addition 13 of steam to ethene and by fermentation. showsabout an advantage andseries a disadvantage of using the catalytic addition of steam to 36 Which Which row statement homologous is not correct? ethene compared to fermentation? A Alkenes have the same general formula, CnH2n+2. advantage disadvantage B Each member of the homologous series of alkanes differs from the next by CH2. A fast the product is impure C The members of a homologous series all have similar chemical properties. B fast uses non-renewable materials D The members of a homologous series all have the same functional group. C the product is pure slow D diagram usesshows renewable materials slow 37 The part of the molecule of a polymer. H H H H 8 2017 JUN P21 Q38 H 15 H H H H C C C C C C C C C 38 Ethanol is manufactured by fermentation or by the catalytic addition of steam to ethene. H H Which statement is correct? H H H H H H H Which diagram shows monomer from which thisthe polymer could be manufactured? A Fermentation usesthe a higher temperature than catalytic addition of steam to ethene. B A B Fermentation uses a non-renewable resource. C H H to ethene produces H H TheHcatalytic addition of steam purerHethanol thanHfermentation. © UCLES 2016 C D 0620/23/O/N/16 H H of steam H H C C C to ethene D HTheCcatalytic addition uses aCbiological catalyst. C H H H 39 The structure of an ester is shown. H H H C O H H 9 2017 JUN P22 Q38 38 Ethanol is manufactured by fermentation H orHby theOcatalytic addition of steam to ethene. H What is an advantage of ethanolHmanufacture instead of by the catalytic addition C fermentation C C by of steam to ethene? O C H H H A Ethanol manufactured by fermentation is purified by distillation. H B Ethanol manufacture by fermentation produces purer ethanol. abul fazal Which row ismanufacture correct? C Ethanol by fermentation uses large areas of land. D Ethanol manufacture by fermentation uses renewable resources. names of the carboxylic acid and name of ester the alcohol used to form the ester 39 The formula of an ester is CH3CH2CH2COOCH2CH2CH3. A methyl propanoate methanoic acid and propanol Which and propanoate alcohol react together to make ester? acid B acid methyl methanol andthe propanoic C D A propyl methanoate acid propyl methanoate butanoic acid methanoic acid and propanol alcohol methanol and propanoic acid butanol B butanoic acid propanol 40 Keratin is a protein that is found in human hair. C propanoic acid butanol Keratin ispropanoic chemicallyacid broken downpropanol to produce amino acids. D What is the name of this chemical process? A catalysis Abul Fazal2017 © UCLES B hydration C hydrolysis 0620/22/M/J/17 Alcohols WS 1 [Turn over 28 14 10 2017 JUN P23 Q38 38 Ethanol can be produced by fermentation or by the catalytic addition of steam to ethene. Which row shows an advantage and a disadvantage for each process? catalytic addition of steam to ethene fermentation advantage disadvantage 13 advantage disadvantage batch slow continuous 37 X,AY and Z are three hydrocarbons. process reaction process X CH2=CH2 Y CH3–CH=CH2 Z fast continuous pure ethanol B reaction X, Y and process What do compounds Z have in common?formed C renewable batch 1raw They are all alkenes. material process D 2 renewable They are all part of the same homologous impure ethanol fast series. fast reaction CH3–CH2–CH=CH2 renewable raw material pure ethanol formed slow reaction finite raw material material 3raw They all have the formed same boiling point.reaction A 1, 2 and 3 B 1 and 2 only 39 The structure of an ester is shown. C 1 and 3 only D 2 and 3 only 11 2017 NOV P23 Q38 H H 38 The diagram shows a reaction sequence. butane X H C C ethene H H O H C Y O 14 H ethanol C C H Z carbon dioxide and water H H Which row names the processes X, Y and Z? 37 Three chemical reactions are shown. Which alcohol and carboxylic acid produce this ester? X Y Z 1 catalytic addition of steam to ethene alcohol carboxylic A fermentation 2 cracking combustion of ethanol acid respiration B A abul fazal cracking hydration acid combustion 3 ethanol fermentation of ethanoic glucose C distillation fermentation B ethanol propanoic acid respiration In which of the reactions does the relative molecular mass of the carbon-containing compound D distillation hydration C propanol ethanoic acid combustion decrease? propanoic acid A D 1 and 2propanol B 1 only C 39 The structure of an ester is shown. 2 and 3 D 3 only 12 2018 MAR P22 Q38 40 How the amino acids in protein and identified? 38 How can is ethanol produced byafermentation? H H be separated O A A Add locating agent to theCprotein. H C °CC usinga anaerobic conditions at 30 H H B B Hydrolyse the protein and then use chromatography. using anaerobic conditions H at 450 H °C O C C C C H H H C Polymerise the protein and then add a locating agent. C using steam at 30 °C H H H H D Use chromatography on a solution of the protein. °C D using steam at of 450 Which combination carboxylic acid and alcohol produces this ester? carboxylicreact acid together toalcohol 39 Which substances form ethyl propanoate? butanoic acidpropanol A A ethanoic acid and butanoic acid © UCLES B B2017 ethanol and propene C ethanoic acid C ethene and propanol Alcohols WS 1 D propanoic acid D propanoic acid and ethanol ethanol propanol 0620/23/M/J/17 butanol butanol Abul Fazal 29 12 13 2018 JUN P21 Q38 38 Ethanol is produced by fermentation or from ethene. What is a disadvantage of producing ethanol by fermentation? A Distillation is needed to purify the ethanol produced. B Fermentation uses glucose from plants. C Fermentation is catalysed by enzymes in yeast. D Fermentation occurs at a low temperature and pressure. 12 39 Which structural formula represents methyl propanoate? 14 2018 JUN P22 Q38 38 A TwoCH processes used3 for the large-scale production of ethanol are shown. 3CH2COOCH B CH3COOCH process2CH 1 2CH A 3compound containing carbon, hydrogen and oxygen is used to produce C ethanol. CH3CH2CH2COOCH 3 D process 2 A compound containing carbon and hydrogen only is used to produce HCOOCH 2CH2CH3 ethanol. Which row statement is correct? 40 Which describes addition polymerisation and condensation polymerisation? A Process 1 uses a renewable starting material. addition polymerisation condensation polymerisation B Process 1 is done at a very high temperature. A monomers have a C=C double bond monomers have a C=C double bond and the polymerfermentation. is the only product and the polymer is the only product C Process 2 involves monomers haveataroom C=C temperature. double bond D B Process 2 is done and the polymer is the only product C the monomers react to form the the monomers react to form the polymer and a small molecule 13 monomers have a C=C double bond 39 2018 What is thepolymer nameQ38 ofand the aorganic product of the reaction shown? small molecule and the polymer is the only product JUN P23 15 38 Which describes an advantage andthe a disadvantage of making ethanol fermentation? + CH3CH → D row the monomers react toCH form the2OH monomers react to by form the 3COOH polymer and a small molecule polymer and a small molecule disadvantage A ethyl ethanoateadvantage abul fazal B A ethyl methanoate uses a renewable resource occurs at a slow rate needs a high temperature C B methyl ethanoate produces impure ethanol as a product produces pure ethanol as a product D C methyl propanoate D occurs at a slow rate needs a high temperature uses a non-renewable resource 40 Which two compounds react together to form a condensation polymer? 39 Which esters have formula C5H10O2? andmolecular CH3COOH A HOCH 2CH 2OHthe B and CH3NH2 HOCH 2OH 1 2CH ethyl propanoate C and H2NCH2CH2NH2 HOCH 2OH ethanoate 2 2CH propyl D HOCH and HOOCCH2CH2COOH 2OH 3 2CH butyl methanoate 4 methyl butanoate A 1, 2, 3 and 4 B 1, 2 and 3 only C 1 and 2 only © UCLES 2018 Abul Fazal D 3 and 4 only 0620/21/M/J/18 Alcohols WS 1 30 15 16 2018 NOV P22 Q38 38 Ethanol is manufactured from ethene. What is an advantage of this process? A It is a continuous process. B It has high labour costs. C It needs high temperature and pressure. D It uses non-renewable materials. 14 39 2018 WhichNOV reaction be used to make ethanoic acid? 17 P23can Q38 38 Sugar can be fermented to produce ethanol. A oxidation of ethanol Some of the stages in the process to produce and purify ethanol are listed. B oxidation of ethene C 1 Leave in a warm place. reduction of ethanol D 2 Add reduction of yeast. ethene 3 Fractionally distil the solution. 4 Dissolve the sugar in water. 40 The structure of an addition polymer is shown. 5 6 Filter to remove the yeast. H OH H Crush some sugar cane. C C What is the correct order of these stages? A H 4→6→2→1→5→3 H OH H OH C C C C H H H H Which monomer used B 6→ 4 → 1 → is 2→ 5 →to3make this polymer? abul fazal C 6 → 4 →A2 → 1 → 3 → 5 B C D 6 → 4 →OH 2→1→5→3 OH OH D H H C H H 13 H C C 39 Which statement about ethanoic acid is correct? 18 2021 JUN P22 Q34 H a –C 34 Which statement about ethanol isHnotHcorrect? A It contains 2H5 group. OH C H C C HO H B A It is a strong Ethanol can acid. be made by fermentation. C B It is formed by the reduction ethanol.acid. Ethanol is oxidised to make of ethanoic D C It reacts reacts with alcohols to formexothermically, esters. Ethanol with oxygen making it a good fuel. H C H OH D Ethanol reacts with propanoic acid to make propyl ethanoate. 40 The structure of a polymer is shown. 35 Which pair of formulae represents H twoClalkanes? H Cl A CH4 and C8H18 C C C C H Cl C C Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every C5Hby B effort C2H 6 and 8 the publisher (UCLES) reasonable has been made trace copyright H to Cl H Clholders, H but ifClany items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. C C3H6 and C5H12 To avoid the issue of disclosure of answer-related to candidates, all copyright acknowledgements are reproduced online in the Cambridge Which monomer is used to makeinformation this polymer? International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at H and C H D C 10 the 8 live examination 4 8 www.cie.org.uk after series. B D C Alcohols WS 1 A Abul Fazal Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. H isClcorrect? Cl Cl about Cl 36 Which statement alkanes © UCLES 2018 Cl H 0620/22/O/N/18 Cl H Cl H A production of sulfur dioxide 2 manufacture of iron gas B production of sulfur trioxide 3 treating alkaline soilsgas C production oleum Which metal is of used make the anodes? Which suggestions aretocorrect? D A A 31 production of concentrated sulfuric acid 1calcium and 2 only B 1 and 3 only C 2 and 3 only 19 2020 JUN P21 Q35 D 1, 2 and 3 B copper 35 Which row about the production of ethanol by fermentation is correct? 34 One of the reactions used in the manufacture of sulfuric acid is shown. C sodium zinc raw materials D energy + O2 2SO3 rate of reaction 2SO2requirement A catalyst non-renewable high Which is used to increase the rate of this reaction? slow 33 A B student suggests three uses of calcium renewable lowcarbonate (limestone). slow A iron 1non-renewable manufacture IV) oxide of cement B C manganese( low fast 2 renewable manufacture of iron C D vanadium( V) oxide high fast D nickel3 treating alkaline soils 36 Which statement about homologous series is correct? 20 2020 P22 Q35 WhichJUN suggestions are correct? 35 A Ethanol is made an industrial series scale by thethe fermentation of sugars or by the reaction of ethene Members of on a homologous have same structural formula. A steam 1 and 2 B 1 of and 3 only catalyst. C 2 and 3 only D 1, 2 and 3 with in only the presence a suitable B Members of a homologous series all have similar chemical properties. What is a disadvantage of making ethanol from ethene rather than by fermentation? Members homologous series all have similar properties. V) oxide? 34 C Which reactionofina the Contact process is catalysed by physical vanadium( A A continuous production process is used. D Members of all homologous series are hydrocarbons. A S(s) + O2(g) → SO2(g) B A non-renewable raw material is used. O2very (g) → 2SO3(g) B The 2SOproduct 2(g) + is C pure. C D SO3rate (g) +of H H2high. S2O7(l) 2SO4(l)is→ The reaction very D H2S2O7(l) + H2O(l) → 2H2SO4(l) 36 2020 Which JUN statement P23about Q35 compounds in the same homologous series is correct? 21 35 A Ethanol produced by: chemical properties because they have the same number of carbon Theyishave the same atoms. 1 the catalytic addition of steam to ethene B They have the same physical properties because they have the same number of carbon 2 fermentation. atoms. abul fazal © UCLES 0620/21/M/J/20 over C 2020 They have different chemical properties because they have different numbers of [Turn carbon Which statement is correct? atoms. A Both processes require similar amounts of energy. D They have different physical properties because they have different numbers of carbon B atoms. Both processes use a catalyst. C Process 1 uses a renewable resource. D Process 2 produces the purest ethanol. © © UCLES UCLES 2020 2020 Abul Fazal 0620/22/M/J/20 0620/23/M/J/20 [Turn over Alcohols WS 1 D methyl 2 methanoate Propene decolourises bromine water. 3 Propene is obtained by cracking. 35 Which statement about homologous series and isomerism is correct? 4 Propene is a hydrocarbon. 32 A Butane and butene are structural isomers. A 1 and 4 B 2, 3 and 4 C 2 and 4 only D 4 only B Compounds the same homologous series have the same general formula. 22 2020 MAR P22 in Q37 37 C Which row describes thesame production of ethanol and its properties? Compounds in the homologous series 12 have the same molecular formula. 13 formulae. D Structural isomers have different molecular can be made can be molecules made isare used as a is used as a 35 The structures of four organic shown. from glucose from ethene fuel solvent 36 The fractional distillation of petroleum is shown. 36 Which is correct? A H statement about alkanes gas key O H refinery H A B They burn in oxygen. = yes H C Cl H C O H H C C O H = no B C They contain carbon, hydrogen and oxygen atoms. H H gasoline H fraction C D They contain double bonds. H O H C H H D bonds. series are represented byparaffin fraction HowThey manycontain differentionic homologous these molecules? 23 2021 A 1 JUN P21 Q37 B 2 C 3 D 4 diesel oil 37 What is an advantage of manufacturing ethanol by fermentation? The processabout is very fast. is correct? 36 A Which statement ethene petroleum © UCLES 2020 0620/22/F/M/20 B The requires no separation. A It hasethanol the chemical formula C2H6. C B lubricating fraction [Turn over The rawinmaterials used are renewable. It burns excess oxygen producing carbon dioxide and water. bitumen orange solution. It reactsare with There noBr other productsanformed. 2 to produce C D Which fractionwith is the least to volatile? D It reacts oxygen form ethanol. A bitumen 24 2021 NOV P22 Q37 37 B Ethanol is oil manufactured by fermentation of sugars or by catalytic hydration of ethene. diesel C gasoline fraction Which row states an advantage of each method? D refinery gas fermentation hydration A statement produces purer ethanol is series a batchisprocess 37 Which about members of a homologous correct? abul fazal produces purer ethanol is a continuous process Successive members differ by CH3. C uses a renewable resource is a batch process B Successive members have a molecular mass that differs by 14. © UCLES 2021 0620/21/M/J/21 D uses a renewable resource is a continuous process C They have the same molecular formula. A B D They have identical physical properties. 38 Which statements about unsaturated hydrocarbons are correct? 25 2019 MAR P22 Q38 38 Ethanol is1 manufactured onboth a large scale bydouble fermentation. They contain single and bonds. 2 They turn fermentation aqueous bromine from colourless to brown. Which statement about is correct? A They canprocess. be manufactured by cracking. It is a3continuous B A A 1 renewable and 2 only rawBmaterial 1 andis3used. only C It is a very fast reaction. D The ethanol produced is pure. C 2 and 3 only Alcohols WS 1 UCLES 2019 2021 © UCLES 0620/22/O/N/21 0620/22/F/M/19 D 1, 2 and 3 Abul Fazal [Turn over 33 12 26 2019 NOV P21 Q38 38 Ethanol is manufactured by the catalytic addition of steam to ethene and by fermentation. Which statement describes an advantage of fermentation compared to the catalytic addition of steam to ethene? A Fermentation is a more rapid reaction. B Fermentation produces a purer product. C Fermentation uses a higher temperature. D Fermentation uses renewable resources. 14 39 The diagram shows the structure of a monomer and of the polymer made from it. 27 2019 NOV P22 Q38 38 Ethanol is produced by fermentation or by the reaction of ethene with steam. H H H H Which row is correct? n C C by fermentation H H A uses a temperature of 100 °C What are the monomer and polymer? B needs yeast as a catalyst C C HfromH ethene n uses a temperature of 350 °C does not need a catalyst C very slow reaction monomer polymer very fast reaction D A high yield of ethanol ethane poly(ethane) low yield of ethanol B ethane poly(ethene) 13and of the polymer made from it. 39 The diagram shows the structure of a monomer poly(ethane) C NOVethene P23 Q38 28 2019 D ethene poly(ethene) 38 Ethanol is made by fermentation of sugars and by the catalytic addition of steam to ethene. H H H H What are two advantages of making ethanol by the catalytic addition of steam to ethene rather n C C C C bypolymers fermentation of sugars? 40 than Which possess the same linkage? abul fazal H H faster and reaction and renewable raw materials nylon protein A H H n B protein purer product and faster reaction and starch What are the monomer and polymer? and nylon C starch renewable raw materials and continuous process monomer polymer D nylon and Terylene uses more energy and forms a purer product A ethane poly(ethane) 39 The shows the structure of a monomer and of the polymer made from it. B diagramethane poly(ethene) C ethene D ethene poly(ethane) H H poly(ethene) n C C H H C C H H polymer, X, is shown. H H 40 The structure of a naturally occurring O H What are the monomer and polymer? C C N N monomer polymer O H © UCLES 2019 0620/21/O/N/19 A ethane poly(ethane) What is X? B ethane poly(ethene) Abul Fazal A an amino acid C ethene poly(ethane) B a carbohydrate D ethene poly(ethene) n H O N C Alcohols WS 1 A CH3CH2OH B CH3CH2CH2OH C CH3COOH D CH3CH2COOH 34 29 2020 NOV P23 Q38 38 The flow chart shows the preparation of ethanol and some important chemistry of ethanol. fermentation substance X process Y ethanol carbon dioxide + substance Z What are X, Y and Z? X Y Z A yeast combustion oxygen B glucose combustion steam C glucose polymerisation 13 water D much hydrogen yeast is needed fermentation 37 How to react completelyglucose with 0.02 moles of butene to make butane? B 0.48 dm3 C 0.96 dm3 D 1.20 dm3 A 0.24 dm3 39 Which equation represents the formation of poly(propene) from propene? 30 2021 JUN P23 Q38 38 What is an advantage compared with the A of the fermentation process for producing ethanol B catalytic addition of steam to ethene? CH3 H H H H H CH3 H A Fermentation requires less heat energy. n C n C C C C C C C B Ethanol from fermentation needs to be distilled. C H materials H H H are Raw for fermentation n non-renewable. H H D The fermentation process is carried out in batches rather than continuously. C O C H C H H n D 39 The structure polymer is shown. CH3 H of a synthetic CH 3 H n C OC H C N C O N H n H C CH3 H n OC C C N H H N H H H H H OC C C C H H abul fazal H H H n The structure shows that it is a ......1...... . It is formed by ......2...... polymerisation. Which words complete gaps 1 and 2? 1 2 polyamide addition B polyamide condensation C polyester addition D polyester condensation A © UCLES 2020 0620/23/O/N/20 [Turn over 40 Which substance is a natural polymer? A ethene B Terylene C nylon D protein Alcohols WS 1 Abul Fazal 3 X CH3CH2OH 2 A Z oil lubricating fraction 3 diesel CH3COOH 35 lubricating fraction diesel oil 4 CH CH CH OH B 3 2 C A Y paraffin paraffin lubricating fraction diesel oil Acids Esters WS 14 1, 2 and 4 and C 1, 3 and 4 D 2, 3 and 2 paraffin 1, 2 and 3 B D paraffin diesel oil 1 2016 MAR P22 Q37 lubricating fraction 37 Which compounds contain the same number of carbon, hydrogen and oxygen atoms? 36 Which compound is not an alkane, CnH2n+2? W X Y Z A CH3CH2CH2CH3 ethyl methanoate methyl ethanoate methyl methanoate ethyl ethanoate B (CH3)2CHCH3 A C W and X CH 3CHCHCH 3 B W and Y C X and Z D Y and Z D (CH3)3CH 38 What is an advantage of producing ethanol by fermentation of sugar compared to the catalytic 2 2016 JUN P22 Q37 addition of steam to ethene? 37 An ester is formed when a carboxylic acid reacts with an alcohol. A The alcohol produced is purer. Which ester is formed when propanoic acid and ethanol react? B The process is faster. A CH3CO2CH2CH3 C The process uses high temperature. B CH3CO2CH2CH2CH3 15 D The process uses renewable raw materials. C CH3CH2CO2CH3 36 Which compound does not belong to the same homologous series as the other three D CH3CH2CO2CH2CH3 compounds? CH3OH A B C2H5COOH C C2H5OH D C7H15OH 3 2016 JUN P23 Q37 37 The structure of an alkene and the structure of an ester are shown. P © UCLES 2016 H Q H H H H C C C C 0620/22/M/J/16 H H H C C H H H H H O C O H H C C H H abul fazal H What are the names of P and Q? P Q A but-1-ene ethyl propanoate B but-1-ene propyl ethanoate C but-2-ene ethyl propanoate but-2-ene 0620/21/M/J/16 propyl ethanoate © UCLES D2016 [Turn over 38 What is an advantage of producing ethanol by fermentation of sugar compared to the catalytic addition of steam to ethene? A The alcohol produced is purer. B The process is faster. C The process uses high temperature. D The process uses renewable raw materials. Abul Fazal Acids and Esters WS 1 D A reaction general with steam B general different functional group decrease similar electronic structure increase C general functional group 36 Ethanol is a fuel used in cars. It cansimilar be made36 from petroleum. increase D molecular similar functional group increase cracking C4H10 → C2H4 + C2H6 13 4 2016 MAR P22 Q38 producing ethanol C2H4 + H2O → C2H5OH 38 Which structure represents a compound that dissolves in water to form an acidic solution? 35 Which equation representing a reaction of methane is correct? C2H5OH + 3O2 → 2CO2 + 3H2O burning A B A CH4 + Cl 2 → CH3Cl + HCl Compounds of how many homologous series appear in these equations? H H H H H H B CH4 + Cl 2 → CH4Cl 2 A 1 B 2 C 3 D 4 H C 2 +C H2 C H C C C C CH4 + Cl 2 → HCH2Cl H 2 +orHsugar. Heither D 2CHis4 produced + 2Cl 2 →from 2CH Cl 3ClH +ethene 2 37 Ethanol H H Which type of chemical reaction is used in each case? 36 Which two compounds are molecules which both contain a double bond? C D ethene → ethanol sugar → ethanol A ethane and ethanoic H H H Hacid H H O addition fermentation B A ethane and ethanol H C C C H C C C C O H addition fractional distillation C B ethene and ethanoic acid O H H H H H H distillation fermentation D C ethene and ethanol D distillation H fractional distillation 37 Ethanol can be formed by: 5 2017 MAR P22 Q38 38 The structural formula of an organic compound is shown. 1 fermentation 2 reaction between steam and CH2COOCH3 CH3ethene. Whichisofthe these processes use a catalyst? What name of this compound? butanoic 1 acid 2 B A ethyl ethanoate A C B methyl propanoate D C propyl methanoate D abul fazal 6 2018 NOV P21 Q38 0620/22/F/M/16 [Turn over 38 When the alcohol CH3CH2CH2OH reacts with the carboxylic acid CH3CH2CH2COOH an ester is formed. © UCLES 2016 What is the name and structural formula of this ester? name 0620/22/F/M/17 structural formula A butyl propanoate CH3CH2COOCH2CH2CH2CH3 B butyl propanoate CH3CH2CH2COOCH2CH2CH3 C propyl butanoate CH3CH2COOCH2CH2CH2CH3 D propyl butanoate CH3CH2CH2COOCH2CH2CH3 © UCLES 2017 © UCLES 2018 Acids and Esters WS 1 0620/21/O/N/18 [Turn over Abul Fazal A Fermentation uses a higher temperature than the catalytic addition of steam to ethene. uses resource. 37 B The Fermentation diagram shows partaofnon-renewable the molecule of a polymer. The catalytic addition of steam to ethene 37 produces purer ethanol than fermentation. H H H H H H H H H The catalytic addition of steam to ethene uses a biological catalyst. C C C C C C C C C C D 7 2017 JUN P21 Q39 H H 39 The structure of an ester H is shown. H H H H H H Which diagram shows the monomer from this polymer could be manufactured? H which H O A BH H H C H H H Which row is correct? H C C H C H H C H H H H C C H O C C D HH H H C H H H H C C H H O H names oforthe acid and of steam to ethene. 38 Ethanol is manufactured by fermentation bycarboxylic the catalytic addition name of ester the alcohol used to form the ester What is an advantage of ethanol manufacture by fermentation instead of by the catalytic addition propanoate methanoic acid and propanol of A steammethyl to ethene? methyl propanoateby fermentation methanolisand propanoic acid A B Ethanol manufactured purified by distillation. propyl methanoate methanoic acid and propanol B C Ethanol manufacture by fermentation produces purer ethanol. propyl methanoate methanol andlarge propanoic acid C D Ethanol manufacture by fermentation uses areas of land. D Ethanol manufacture by fermentation uses renewable resources. 40 Keratin is a P22 protein that is found in human hair. 8 2017 JUN Q39 39 Keratin The formula of an ester is CHdown COOCHamino 3CH2CH 2CH2CH 3. is chemically broken to 2produce acids. Whichisacid alcohol together to make the ester? What the and name of thisreact chemical process? A catalysis acid alcohol B A hydration butanoic acid butanol C B hydrolysis butanoic acid propanol D C polymerisation propanoic acid butanol D abul fazal propanoic acid propanol Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. © UCLES 2017 0620/22/M/J/17 [Turn over To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at www.cie.org.uk after the live examination series. Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2017 Abul Fazal 0620/21/M/J/17 Acids and Esters WS 1 batch pure Y CH3–CH=CH Xrenewable CH2=CH2 2 ethanol Z raw material process formed What do compounds X, Y and Z have in common? 38 renewable impure ethanol fast D raw material formed reaction 1 They are all alkenes. slow2–CH=CH2 CH3–CH reaction C finite raw material 2 P23 They are all part of the same homologous series. 9 2017 JUN Q39 39 The structure of an ester is shown. 3 They all have the same boiling point. A 1, 2 and 3 B H H 1 and 2 only C H C 1Oand 3 only H H C C 38 The diagram shows a reaction sequence. H H O C D C 2 and 3 only H X Y H H butane ethene ethanol Which alcohol and carboxylic acid produce this ester? Z carbon dioxide and water Which row names the processes X, Y and Z? alcohol carboxylic acid A X ethanol Y ethanoic acid Z B A ethanol cracking propanoic acid respiration fermentation C B propanol cracking ethanoic acid combustion hydration D C propanol distillation propanoic acid respiration fermentation D distillation hydration combustion 40 How can the amino acids in a protein be separated and identified? 10 2017 NOV P21 Q39 A Add a locating agent tocan thebe protein. 39 Which pair of compounds used to prepare CH3CH2COOCH2CH3? B A Hydrolyseacid the and protein and then use chromatography. ethanoic ethanol C B Polymerise theand protein and then add a locating agent. ethanoic acid propanol D C Use chromatography on a solution of the protein. propanoic acid and ethanol D propanoic acid and propanol 13 abul fazal 11 2017 NOV P22 Q39 The structure of an ester is shown. ©39 UCLES 2017 © UCLES H [Turn over 0620/23/M/J/17 0620/21/O/N/17 H H O C C C H H O H H C C H H H Which substances react to form this ester? A ethanol and ethanoic acid B ethanol and propanoic acid C propanol and ethanoic acid D propanol and propanoic acid 40 A polymer can be made from methyl propene. H CH3 C Acids and Esters WS 1 H C CH3 Which diagram shows the structure of the polymer? Abul Fazal A cracking fermentation respiration B cracking hydration combustion C distillation fermentation 39 respiration D distillation hydration combustion 14 12 2017 NOV P23 Q39 39 Three The structure of reactions an ester isare shown. 37 chemical shown. 1 H catalytic additionHof steam toOethene 2 combustionHof ethanol C C 3 fermentation of glucose H H C O H H H H C C C C H In which of the reactions does the relative molecular of the carbon-containing compound H H mass H H decrease? Which combination of carboxylic acid and alcohol produces this ester? A 1 and 2 B 1 only C 2 and 3 D 3 only carboxylic acid alcohol 38 How produced A is ethanol butanoic acid by fermentation? ethanol A B using butanoic anaerobicacid conditions at propanol 30 °C butanol °C B C using ethanoic anaerobicacid conditions at 450 acid C D usingpropanoic steam at 30 °C butanol using steam at 450 °C D 12 13 2018 MAR P22 Q39 39 Ethanol Which substances together to or form ethyl propanoate? 38 is producedreact by fermentation from ethene. © UCLES 2017 [Turn over 0620/23/O/N/17 A ethanoic acid and propanol What is a disadvantage of producing ethanol by fermentation? B A ethanol and Distillation is propene needed to purify the ethanol produced. C B ethene and propanol Fermentation uses glucose from plants. D C propanoic acid ethanol Fermentation is and catalysed by enzymes in yeast. D Fermentation occurs at a low temperature and pressure. 40 The structure of a chlorofluorocarbon polymer is shown. abul fazal 14 2018 JUN P21 Q39 39 Which structural formula represents methyl CH propanoate? Cl CH Cl 3 A CH3CH2COOCH3 B CH3COOCH2CH2CH3 C C H F H C CH3CH2CH2COOCH3 Which monomer is used to make this polymer? D HCOOCH2CH2CH3 F A C 3 C B C D 40 Which row describes polymerisation polymerisation? CH3addition Cl H Cl and condensation CH3 F CH3 H C Cpolymerisation C addition C Ccondensation C C C polymerisation A monomers CH3 bond F have H a C=C double F and the polymer is the only product monomers bond Cl H have a C=C Cl double F and the polymer is the only product B monomers have a C=C double bond and the polymer is the only product the monomers react to form the polymer and a small molecule C the monomers react to form the polymer and a small molecule monomers have a C=C double bond and the polymer is the only product D the monomers react to form the the monomers react to form the polymer and a small molecule 0620/22/F/M/18polymer and a small molecule Acids and Esters WS 1 © UCLES 2018 Abul Fazal A Process 1 uses a renewable starting material. B Process 1 is done at a very high temperature. C Process 2 involves fermentation. D Process 2 is done at room temperature. 40 15 2018 JUN P22 Q39 13reaction shown? 39 What is the name of the organic product of the 38 Which row describes an advantage a disadvantage of making ethanol by fermentation? COOH + CH CH OH → CH and 3 3 2 ethyl ethanoateadvantage A disadvantage B A ethyl methanoate uses a renewable resource occurs at a slow rate needs a high temperature C B methyl ethanoate produces impure ethanol as a product produces pure ethanol as a product D C methyl propanoate D needs a high temperature occurs at a slow rate uses a non-renewable resource 40 2018 WhichJUN two compounds 16 P23 Q39 react together to form a condensation polymer? 39 Which esters have the molecular formula C5H10O2? A HOCH 2CH2OH and CH3COOH B and CH3NH2 HOCH 1 2CH ethyl propanoate 2OH C and H2NCH2CH2NH2 HOCH 2 2CH propyl 2OH ethanoate D HOCH and HOOCCH2CH2COOH 3 2CH butyl methanoate 2OH 4 methyl butanoate A 1, 2, 3 and 4 B 1, 2 and 3 only C 1 and 2 only D 3 and 4 only 40 A polymer linkage contains carbon, hydrogen,14 nitrogen and oxygen atoms. 17 2018 NOV P21 Q39 15 39 Which A solution ethanol water left to stand in an open beaker in a warm room for three weeks. row of about the and polymer is is correct? abul fazal 38 Ethanol is manufactured from ethene. Which statement explains what happens to the ethanol in the solution? type of formed by What is anpolymer advantage of this process? A The ethanol is dehydrated to ethene. AA The It is ethanol apolyamide continuous process. addition polymerisation B is hydrolysed to ethene. BB2018 It has high labour costs. polyamide condensation polymerisation C The ethanol is oxidised to ethanoic acid. © UCLES 0620/22/M/J/18 polyester addition polymerisation CC The It needs high temperature and pressure. D ethanol is reduced to ethanoic acid. polyester DD It uses non-renewablecondensation materials. polymerisation 40 2018 The structure of aQ39 polymer is shown. NOV P22 18 39 Which reaction can be used to make ethanoic acid? H CH CH CH3 3 H 3 H A oxidation of ethanol C C B oxidation of ethene H CH3 H C reduction of ethanol D reduction of ethene C C C C CH3 H CH3 Which monomer is used to make this polymer? A B C CH CH3 H 3 CH 3 40 The structure of an addition polymer is shown. Acids and2018 Esters WS 1C © UCLES C C H H H H C H C 0620/23/M/J/18 C OH H CH3 C C D C OH H CH3 H C CH3 H CH3 C OH C C C CH3 H Abul Fazal B 6→4→1→2→5→3 C 6→4→2→1→3→5 D 6→4→2→1→5→3 41 19 2018 NOV P23 Q39 39 Which statement about ethanoic acid is correct? A It contains a –C2H5 group. B It is a strong acid. C It is formed by the reduction of ethanol. D It reacts with alcohols to form esters. 11 40 2021 The structure of Q33 a polymer is shown. 20 NOV P22 33 What is the structure of the ester formed acid Cl and propanol? H ClfromHethanoic Cl H A C C H Cl H Cl H H H C C C Which monomer is used to make this polymer? O C C H H H A B H H Cl H Cl Cl Cl Cl H H Cl H H C C H C H H Cl H C C C Cl H D H C C H H C Cl H C H C O C H C B C H C C C Cl H C Cl H O C H H C C H O C H C H H H D C O H Cl H C H C Cl H O C O H H H C C C H H H abul fazal © UCLES 2018 H H C H H H C 0620/23/O/N/18 H O H 34 Fuel X produces carbon dioxide and water when it is burned in air. So does fuel Y. What could X and Y be? X Y A C H2 B C C8H18 C CH4 H2 D CH4 C8H18 Abul Fazal Acids and Esters WS 1 42 12 21 2021 JUN P21 Q34 34 Compound Z contains carbon, hydrogen and oxygen. Molecules of compound Z have four hydrogen atoms and two carbon atoms. Compound Z can be made by oxidation of an alcohol. What is compound Z? A ethene B ethanol C ethanoic acid D methyl methanoate 12 35 2021 WhichJUN statement about homologous series and isomerism is correct? 22 P23 Q34 34 Ethanol is reacted with acidified potassium manganate(VII). A Butane and butene are structural isomers. Which row describes thesame type of reaction and the type of the organic formed? B Compounds in the homologous series have samecompound general formula. C Compounds in the same homologous series have the same molecular formula. type of reaction organic compound D Structural isomers have different molecular formulae. A oxidation carboxylic acid B oxidation alkene 36 Which statement about alkanes is correct? C dehydration carboxylic acid A They burn in oxygen. D dehydration alkene B They contain carbon, hydrogen and oxygen atoms. C diagrams They contain bonds. formulae of13 35 The showdouble the structural four compounds. 23 2020 NOV P23 Q37 Theyiscontain ionic bonds. 37 D Propanol oxidised by acidified potassium manganate(VII) in a similar 1 2 way to ethanol. abul fazal H H by the oxidation ofH propanol with H acidified H H His H Which compound produced potassium 37 What is an advantage of manufacturing ethanol by fermentation? manganate( VII)? H C C C C C H H C C C C C H A CH The3CH process 2OH is very fast. H H H H H H H H H B CH The3CH ethanol requires no separation. 2CH2OH H C H C CH The3COOH raw materials used are renewable. H D CH There no other products formed. 3CHare 2COOH 3 4 38 The flow chart shows the preparation of ethanol and some important chemistry of ethanol. H H H H H H H H H substanceHX fermentation C C C C ethanol H process Y H C +Csubstance H C carbon C Cdioxide Z H H H Z? H H H What are X, Y and H C H H C X Y Z H H A yeast combustion oxygen Which two compounds are structural isomers? B glucose combustion steam Acids A and 1 Esters and 3WS 1 B 1 and 4 C 2 and 3 D 2 and 4 glucose polymerisation 0620/21/M/J/21 water © UCLESC2021 D yeast fermentation glucose H H Abul Fazal A B They burn oxygen. Ethanol caninbe made from ethene but propane is obtained from petroleum. B C They contain carbon, hydrogenis and oxygen atoms. Ethanol is a liquid but propane a gas. C D 43as other alcohols but propane does not. They contain double bonds. Ethanol contains the same functional group D They contain ionic bonds. 37 Chlorine reacts with methane. 24 2021 JUN P22 Q37 37 Which Which statements statementsare about ethanoic acid are correct? correct? 11 It is reaction a strong takes acid. place in the dark. The 22 It reacts withofethanol towith formmethane an ester.forms chloromethane. The reaction chlorine 33 COOH. It has the formula CH3with Chloromethane reacts chlorine to produce dichloromethane. 15 4 2 only The reaction chlorine methane addition 1 and B 1ofand 3 onlywith C 2 andis3an only D reaction. 1, 2 and 3 A 1 and 2 B homologous 1 and 3 C is 2not and 3 36 A Which statement about series correct? D 3 and 4 25 2019 P21 Q38 A AllJUN homologous series are hydrocarbons. 38 Which statements about aqueous ethanoic acid are correct? B Members of a homologous series have the same functional group. C 1 Ethanoic acid contains the functional –COOH. Members of a homologous series have similar group chemical properties. D Ethanoic acid reactsof with carbonates series. to produce hydrogen. The 2alkanes are an example a homologous 13 3 Ethanoic acid turns Universal Indicator paper blue. 37 Which In bright ethane and chlorine combine substitution reactions. 36 statements about homologous series are in correct? 4sunlight, Ethanoic acid has a pH lower than pH 7. Which compound is B not formed in these reactions? 1 2 All members chemical properties. A 1 and 1have and 3similar C 1 and 4 D 2 and 4 molecular B Chave C2H4Clmass. C2H2 3Cl All members 2H5Clthe sameC 2 D HCl A 39 2019 The structure of an ester is shown. 3 P22 Ethane and ethene are members of the same homologous series. JUN Q38 26 38 What are4 theEthane properties aqueous ethanoic acid? andofpropane are members of the same homologous series. O B 1 and 4 CHreacts 2 and 3 D 2 and 4 with 0620/22/M/J/21 [Turn over 3 CC decolourises turns damp red calcium carbonate to bromine water litmus blue 2CH2CH3 make carbonOCH dioxide 37 Which type of reaction takes place when methane reacts with chlorine in the presence of A is the ultraviolet light? What nameof the ester? A 2021 1 and 3 © UCLES abul fazal A B addition ethyl propanoate B C cracking methyl propanoate C D polymerisation propyl ethanoate D substitution propyl methanoate 39 The structures of four molecules are shown. 27 2019 JUN P23 Q38 38 Which 1statement about aqueous ethanoic acid is correct? 2 3 A 4 It reacts to form salts, H H hydrogen H H and water. O with metal carbonates B 2019 It reacts with metal oxides to form salts and oxygen. © UCLES H C OH H0620/21/M/J/19 C C C H C OH H C It reacts with reactive metals to form salts and hydrogen. OH H H H H D It turns damp red litmus paper blue. Which molecules react together to form the ester propyl methanoate? 39 The shown. A structure 1 and 2 of esterBW is 1 and 3 C 2 and 4 H H C H Abul Fazal D H H C C H H O C OH 3 and 4 O H C O C H H Acids and Esters WS 1 Which row gives the names of ester W and the carboxylic acid and alcohol from which it is made? 44 14 37 Increasing the number of atoms in one molecule 14 of a hydrocarbon increases the amount of 28 2020 P22when Q38it burns. energyMAR released 38 Ethanoic acid is a typical carboxylic acid. What is the correct order? 13 Which statement about ethanoic acid is correct? more energy less energy 36 Which statement about a homologous series is correct? A It can released be oxidised to produce ethanol. released A All members have the same general formula. B A It is a proton etheneacceptor. ethane methane B All members have the same molecular formula. C B It is fully dissociated in methane water. ethene ethane C All members have similar physical properties. D C It reacts with ethanol to produce methane ethane ethyl ethanoate ethene and water. D Members show a trend in their chemical properties. D methane ethene ethane 39 Which structure represents the ester made from ethanoic acid and propanol? 29 2020 JUN P22 Q38 37 Increasing the number of atoms in one molecule of a hydrocarbon increases the amount of 38 An organic compound, reacts with zinc to produce a gas, Q. B A P, energy released when it burns. H PH H O What are and Q? What is the correct order? H A B A C PC O less energy released H ethanoic H H acid C D C ethanoic etheneacid C ethanol ethene H Hethanol O methane HD C C B C C O methane C H H H O H C more energy carbon H dioxide released H C C C QH hydrogen ethane methane carbon dioxide methane H H hydrogen ethane ethane C ethene C H ethane H O H H H H C C C H H H H H C C H D ethene H O C C O H 39 Alkanes undergo substitution reactions in the presence of UV light. H H H 30 2020 H JUNHP23 Q38 H H 38 Which A smallequation quantityrepresents of a solid chemical is added to aof large excess of aqueous ethanoic acid. a substitution reaction ethane? 40 A Thebubbles structure a polymer shown. Clof C2seen H4 +isand 2HCl C No gas the solid dissolves to give a colourless solution. 2H6 + of 2 →are B H6 +theClsolid C2H H5Cl + HCl O 2 → chemical? WhatC2was H O N C abul fazal C A C 2H6 + Cl 2 → C2H calcium hydroxide N4Cl 2 + H2 C N C D B C2H6 + HCl → C2H5Cl + H2 copper(II) oxide H O C magnesium Which substances statements are about the polymer are correct? 40 Which natural polymers? D sodium carbonate The polymer is nylon. 11 proteins 2 carbohydrates The polymer is formed by condensation polymerisation. 39 Alkanes 2undergo substitution reactions with chlorine in the presence of ultraviolet light. There are ester linkages between the monomers. 33 nylon Which equation shows a reaction of this type? 4 2 poly(ethene) A 1 and B 2 and 3 C 2 only D 3 only A C3H6 + Cl 2 → C3H6Cl 2 A 1 and 2 B 1 and 3 C 2 and 3 D 3 and 4 B C3H8 + Cl 2 → C3H6Cl 2 + H2 C C3H8 + 2Cl 2 → C3H6Cl 2 + 2HCl D C3H6 + Cl 2 → C3H5Cl + HCl © UCLES 2020 © UCLES 2020 0620/22/M/J/20 0620/22/F/M/20 Acids and Esters WS 1 © UCLES 2020 0620/23/M/J/20 Abul Fazal [Turn over A 5 6 B 5 12 C 6 5 D 12 5 31 2021 MAR P22 Q38 45 38 The formula of an ester is CH3CH2CH2COOCH2CH2CH3. Which acid and alcohol react together to make the ester? acid alcohol A butanoic acid butanol B butanoic acid propanol C propanoic acid butanol D propanoic acid propanol 14 39 Molecule 1 undergoes a process to make molecule 2. 32 2019 MAR P22 Q39 39 The structure of a compound, G, is shown. process molecule 1 G is in the same homologous series as ethanoic acid. molecule 2 Which row describes the molecules and the process? H H O A molecule 1 H process C C monomer cracking H H C 2 O molecule H polymer B monomer polymerisation polymer Which row describes some of the properties of an aqueous solution of G? C small molecule polymerisation monomer D produces a gas small molecule with magnesium turns methyl orange cracking yellow A no yes monomer abul fazal B C D no no yes no yes yes 40 Which statement about polymers is correct? © UCLES 2021 0620/22/F/M/21 [Turn over O A Nylon contains the B Nylon is a polyester. C Propane can be polymerised by addition polymerisation. D The linkage in Terylene contains a carbon-carbon double bond. Abul Fazal C N linkage. H Acids and Esters WS 1 D 2 Ethanoic acid reacts with carbonates to produce hydrogen. Members of a homologous series have the same functional group. 3 Ethanoic acid turns Universal Indicator paper blue. Members of a homologous series have similar chemical properties. 4 Ethanoic acid has a pH lower than 7. 46pHseries. The alkanes are an example of a homologous A 1 and 2 B C B 1 and 3 C 1 and 4 D 2 and 4 37 2019 In bright sunlight, ethane and chlorine combine in substitution reactions. 33 JUN P21 Q39 39 The structure of an ester is shown. Which compound is not formed in these reactions? 13 O B C2H5Cl C C2H4Cl 2 A C2H3Cl 36 Which statements about homologous series are correct? CH3 C D HCl membersofhave similar chemical properties. 38 What are1 theAll properties aqueous ethanoic acid? OCH CH CH 2 2 3 2 All members have the same molecular mass. reacts with What is the decolourises name of the ester? turns damp red 3 Ethane and ethene calcium are members of thetosame homologous series. carbonate bromine water litmus blue make carbon dioxide A ethyl propanoate 4 Ethane and propane are members of the same homologous series. B A methyl propanoate A 1 and 3 B 1 and 4 C 2 and 3 D 2 and 4 C B propyl ethanoate methane reacts with chlorine in the presence of D C propyl 37 Which typemethanoate of reaction takes place when ultraviolet light? D A addition 34 2019 JUN P22 Q39 39 B The cracking structures of four molecules are shown. C 2019 polymerisation © UCLES 1 D substitution O 2 0620/21/M/J/19 3 H H H 4 H H C OH H C C C OH H H C 38 Which statement about aqueous ethanoic acid is correct? OH H H H H A It reacts with metal carbonates to form salts, hydrogen and water. H H C C H H O C OH Which molecules react together formsalts the and esteroxygen. propyl methanoate? B It reacts with metal oxides totoform C A It1 reacts salts2and and 2 with reactive B 1metals and 3 to form C andhydrogen. 4 D D It turns damp red litmus paper blue. 3 and 4 abul fazal 35 2019 JUN P23 Q39 39 The structure of ester W is shown. H H C H O H C O C H H Which the carboxylic acid and alcohol from which it[Turn is made? © UCLES 2019row gives the names of ester W and 0620/22/M/J/19 over name of ester W carboxylic acid alcohol A ethyl methanoate ethanoic acid methanol B ethyl methanoate methanoic acid ethanol C methyl ethanoate ethanoic acid methanol D methyl ethanoate methanoic acid ethanol Acids and Esters WS 1 © UCLES 2019 0620/23/M/J/19 Abul Fazal [Turn over A It can be oxidised to produce ethanol. D H It reacts with ethanol to produceHethyl ethanoate and water. 14 B It is a proton acceptor. 37 Propene is an alkene that reacts with bromine, 47 steam and hydrogen as shown. C It is fully dissociated in water. 36 2020 MAR P22 Q39 C C C H 39 Which structure represents the ester made from ethanoic acid and propanol? H H H B 14 bromine hydrogen steam H H H O H H H O H H H 37 Increasing the number of atoms in one molecule of a hydrocarbon increases the amount of K H Creleased C C C J C H H C LC C O C C C H energy whenOit burns. A What are the products of these reactions? H H order? H isHthe correct H J K more energy less energy C released released H bromopropane H O H H propanol ethene ethane methane dibromopropane propanoic acid C C O Cmethane C ethene C H ethane H dibromopropane propanol ethene H methane H H ethane H bromopropane propanoic acid methane ethene ethane A A B HB C C D D H L butane H O propane C C propane H butane H H H H C C H H H D O H 40 The structure of aQ39 polymer is shown. JUN P22 37 38 2020 The flow chart shows the preparation of ethanol and some important chemistry of ethanol. 38 An organic compound, P, reacts with zinc to produce a gas, Q. H O O fermentation process Y H substance X ethanol carbon dioxide + substance Z What are P and Q? N C N C N C What are X, Y and Z? P Q H O X acid Y dioxide Z A ethanoic carbon Which statements about the polymer are correct? B ethanoic hydrogen A yeast acid combustion oxygen 1 The polymer is nylon. C ethanol carbon dioxide B glucose combustion steam 2 The polymer is formed by condensation polymerisation. D ethanol hydrogen C glucose polymerisation water 3 There are ester linkages between the monomers. D yeast fermentation glucose A 1 and 2 B 2 and 3 C 2 only D 3 only 39 Alkanes undergo substitution reactions in the presence of UV light. abul fazal 38 2020 NOV P21 Q39 39 Which equation statements about aqueous ethanoic acid are represents a substitution reaction of correct? ethane? A → alkane. C2H4 + 2HCl C2H61 + Cl It is2 an B It reacts with sodium carbonate to form carbon dioxide. C2H62 + Cl + HCl 2 → C 2H5Cl C It changes the C2H63 + Cl 2 → C2H 4Clcolour 2 + H2of litmus solution from blue to red. D It is a→ hydrocarbon. C2H5Cl + H2 C2H64 + HCl A 1 and 2 B 1 and 4 C 2 and 3 0620/22/F/M/20 40 Which substances are natural polymers? © UCLES 2020 © UCLES 2020 A 1 proteins 2 carbohydrates 3 nylon 4 poly(ethene) 1 and 2 3 and 4 D 3 and 4 0620/21/O/N/20 B 1 and 3 C 2 and 3 Abul Fazal © UCLES 2020 D Acids and Esters WS 1 0620/22/M/J/20 B condensation C oxidation D substitution 48 39 2021 NOV P21 Q39 39 Which statement about aqueous ethanoic acid is correct? A It reacts with magnesium to produce a salt and hydrogen. B It reacts with sodium hydroxide to produce a salt and hydrogen. C It reacts with ammonium salts to produce ammonia. D It turns red litmus blue. © UCLES 2021 0620/21/O/N/21 abul fazal Acids and Esters WS 1 Abul Fazal Which pair of metals produces the highest voltage? X Y A copper and magnesium A combustion combustion B magnesium and platinum 49 B combustion thermal decomposition C magnesium and zinc C thermal decomposition combustion D silver and platinum D thermal decomposition thermal decomposition Fuels and Cracking WS 1 1 2017 JUN P21 Q11 11 Some properties of four fuels are shown in the table. 33 The ions present in ammonium sulfate are formed from the products of the Contact and Haber Which fuel is a gas at room temperature and makes two products when it burns in a plentiful processes. supply of air? Both of these processes involve the use of a catalyst. Which rowfuel is correct?formula melting point / °C boiling point / °C A hydrogen ion H2 formed –259 from –253 process catalyst B A methane ammonium CH4 –182 ammonia –164 Contact iron C B octane ammonium C8H18 –57 ammonia 126 Haber vanadium(V) oxide D C wax 60 sulfate C31H64 sulfuric acid 400 Contact vanadium(V) oxide Haber iron D sulfate sulfuric acid 2 2017 MAR P22 Q34 34 The table shows the composition of four different types of petroleum. © UCLES 2017 fraction Arabian Heavy /% Arabian Light /% Iranian Heavy /% North Sea /% gasoline 18 21 21 23 kerosene 11 15 13 15 diesel oil 18 0620/21/M/J/17 21 20 24 fuel oil 53 43 46 38 [Turn over Which type of petroleum is best for the motor vehicle industry? A Arabian Heavy B Arabian Light C Iranian Heavy D North Sea abul fazal © UCLES 2017 Abul Fazal 0620/22/F/M/17 [Turn over Fuels and Cracking WS 1 50 12 3 2016 MAR P22 Q35 35 What is the name of fraction X? fractions refinery gas 14 33 One step in the manufacture of sulfuric acid is the oxidation of sulfur dioxide to sulfur trioxide. gasoline Which conditions are used for this step? X temperature / °C pressure / atmospheres catalyst kerosene A 450 1.5 diesel oil iron B 450 1.5 vanadium( V) oxide fraction lubricating C 450 petroleum 200 iron D 450 200 vanadium(V) oxide bitumen A alcohol 34 Which process is used to make lime (calcium oxide) from limestone (calcium carbonate)? fuel oil AB chromatography naphtha BC electrolysis paraffin distillation CD fractional D thermal decomposition 36 Which compounds are alkanes? 4 2016 JUN P23 Q35 35 The diagram shows the separation of petroleum into fractions. compound W X Y formula A C4H10 C5H10 C6H12 Z C6H14 gasoline D Y and Z abul fazal W and X B W and Z C X and Y X Y petroleum Z bitumen What could X, Y and Z represent? X Y Z A diesel oil lubricating fraction paraffin B lubricating fraction diesel oil paraffin C paraffin lubricating fraction diesel oil D 2016 © UCLES paraffin diesel oil0620/22/F/M/16 lubricating fraction Fuels and Cracking WS 1 © UCLES 2016 Abul Fazal 0620/23/M/J/16 33 Sulfuric acid is manufactured by a series of chemical reactions, one of which is catalysed by vanadium(V) oxide. yes no yes no 13 51 What is the equation for the reaction catalysed by vanadium(V) oxide? A D acid. 33 The following scheme shows fourBstages in the conversion C of sulfur to sulfuric A S + O2 → SO2 5 2016 NOV P21 In which stage is aQ35 catalyst used? B 2S + 3O2 → 2SO3 35 Petroleum is an important fossil fuel. A stage B C 2SO2 + O2 → 2SOstage 3 sulfur sulfur Which rowsulfur correctly describes petroleum? dioxide trioxide air D SO3 + H2O → H2SOair 4 type of substance composition A substance compound mainly hydrocarbons 34 Which gives off carbon dioxide on heating? compound A B lime C mixture B limestone D mixture C limewater D slaked lime 36 Butane reacts as shown. stage C only hydrogen and carbon concentrated sulfuric acid mainly hydrocarbons only hydrogen and carbon stage D concentrated sulfuric acid water oleum 6 2016 NOV P22 Q35 34 Petroleum Slaked limeisisseparated used to neutralise ancatalyst acidic soil. 35 into fractions. butane butene + hydrogen and heat How does the pH of the soil change? Which statement is not correct? What is this type of reaction? A Each fraction from contains to a mixture of hydrocarbon molecules. A combustion B A Fuel oil 6burns easily and 7 is used as fuel in cars. B Refinery cracking gas is the fraction containing the smallest molecules. C B 7 8 C polymerisation D C The fractions are separated depending on their boiling point range. 8 7 D D reduction 8 6 7 2016 NOV P23 Q35 35 Which list shows the fractions obtained from distilling petroleum, in order of increasing boiling point? A bitumen → diesel oil → fuel oil → lubricating oil © UCLES 0620/22/O/N/16 B 2016 diesel oil → gasoline → naphtha → kerosene C abul fazal gasoline → naphtha → kerosene → diesel oil © UCLES D 2016 kerosene → lubricating oil → naphtha0620/21/O/N/16 → refinery gas [Turn over © UCLES 2016 [Turn over Abul Fazal 0620/23/O/N/16 Fuels and Cracking WS 1 A It is made by the Haber process. B C It is made in the atmosphere by the action of lightning. 52 It reacts with ammonia to produce a fertiliser. D It reacts with copper metal to produce hydrogen gas. 14 8 2017 JUN P21 Q35 35 Which fraction of petroleum is not matched to its correct use? 34 Statements about methods of manufacture and uses of calcium oxide are shown. 1 fraction use It is manufactured by reacting acids with calcium carbonate. A 2 bitumen It is manufacturedmaking by heating calcium carbonate. roads B 3 gasoline It is used to desulfurise flue gases. fuel for cars C fuel for ships 4 kerosene It is used to treat alkaline soil. D statements naphtha chemical industry Which are correct? A 1 and 2 B 1 and 4 C 2 and 3 D 36 The diagram shows the structures of two organic molecules. 3 and 4 35 The industrial fractional distillation of petroleum is shown. H 9 2017 JUN P22 Q35 H H H C C H H O H H H Hrefinery O gas H C C C C H gasoline fraction H H H naphtha fraction H Which statement about these molecules is not correct? kerosene fraction A They are both alcohols. B diesel oil They both produce carbon dioxide and water when they burn in oxygen. C They contain different functional groups. D They have the same general formula. petroleum Y fuel oil fraction lubricating fraction and bitumen 37 The diagram shows part of the molecule of a polymer. H H Which process happens at Y? H H H H H H H abul fazal A burning B condensation C C C C C C C C C H H H H H H H H H C cracking Which diagram shows the monomer from which this polymer could be manufactured? D evaporation A B C D H H © UCLES 2017 C H H © UCLES 2017 Fuels and Cracking WS 1 H H H C C H H H H H C 0620/22/M/J/17 H H C H H H C C H H O H 0620/21/M/J/17 Abul Fazal 34 The diagram shows the pH values of the soil in two parts of a garden, X and Y. 53 X pH 7.0 10 2017 JUN P23 Q35 13 Y pH 5.5 35 Fuel oil, gasoline, kerosene and naphtha are four fractions obtained from the fractional distillation of petroleum. What the order of the boiling points of these fractions? Lime is used to neutralise the soil in one part of the garden. To whichhighest part ofboiling the garden theboiling lime be added and why? point should → lowest point fuel → naphtha partoil of→ thekerosene garden → gasoline because lime is A fuel oil → kerosene → naphtha → gasoline X acidic gasoline → naphtha → kerosene → fuel oil X basic naphtha → gasoline → kerosene → fuel oil Y acidic 12 D Y basic 36 Limestone Butane andismethylpropane are isomers 34 an important material with with manymolecular uses. formula C4H10. B A C B D C 11 2018 MAR P22 Q35 Which statements aretocorrect? is produce 35 Limestone Statement 1 heated Hydrogen is used......1...... as a fuel.and carbon dioxide. 1 2 They have similar chemical properties. This reaction isWhen called ......2...... . Statement hydrogen burns in the air to form water, heat energy is produced. 2 They have the same general formula. Which correctly complete gaps 1 and 2? Which words is correct? 3 They have the same structural formula. A Both statements 1 are correct and statement 2 2 explains statement 1. A 1, 2 and 3 B 1 and 2 only C 1 and 3 only D 2 and 3 only B A Both statements 2 does not explain statement 1. lime are correct but statement neutralisation C B Statement 1 lime is correct but statement 2 is incorrect. thermal 37 The diagram shows part of the molecule of decomposition a polymer. D C Statement 2 is correct but statement 1 is incorrect. slaked lime neutralisation H H H H H H H H H D slaked lime thermal decomposition C C inCthe same C Chomologous C C series? C C 36 Which row identifies compounds 12 2018 JUN P23 Q35 H of H H H named? H H 35 What is not the correct use the fraction chemical functional H H H properties group Which diagram the monomer from which nameshows of fraction use this polymer could be manufactured? A A B B C CH D D abul fazal different different B fuel oil making waxes C different same H H H gas oil fuel in diesel engines H H similar different C Hkerosene H C C H jet fuel C C similar same naphtha H H H making chemicals H H A D H H H C C H H O H 36 Methane, ethane and propane belong to a family of hydrocarbons called alkanes. What is the general formula of an alkane? A CnH2n © UCLES 2018 B CnH2n+1 C CnH2n–1 0620/22/F/M/18 D CnH2n+2 [Turn over 37 Which substances can be obtained by cracking hydrocarbons? A ethanol and ethene B ethanol and hydrogen © UCLES 2017 C ethene and hydrogen D ethene and poly(ethene) Abul Fazal 0620/23/M/J/17 [Turn over Fuels and Cracking WS 1 34 Some marble chips (calcium carbonate) are heated strongly and substances X and Y are formed. Substance X is a white solid that reacts with water, giving out heat. Substance Y is a colourless 54 gas. What are substances X and Y? 13 13 2017 NOV P21 Q36 X 36 Some of the fractions obtained from Y the fractional distillation of petroleum are used as fuels for vehicles. A calcium chloride oxygen Which two fractions are used ascarbon fuels for vehicles? B calcium hydroxide dioxide calcium oxide carbon dioxide A C bitumen fraction and gasoline fraction calcium sulfate oxygen B D bitumen fraction and naphtha fraction C gasoline fraction and kerosene fraction 35 The structure of compound R is shown. D kerosene fraction and lubricating fraction 37 X, Y and Z are three hydrocarbons.H 14 2017 NOV P22 Q36 X CH2=CH 2 correct?Y 36 Which statement is not H H H C C12 C OH CHH 3–CH=CH 2 H H Z CH3–CH2–CH=CH2 A Petroleum is a mixture of hydrocarbons. What do compounds X, Y and Z have in common? What is R? B The 1mainThey constituent of natural gas is ethane. are all alkenes. A propane C The 2naphtha fraction of petroleum is used for making chemicals. They B propanoic acidare all part of the same homologous series. D When burns air, carbon 3 natural They gas all have theinsame boilingdioxide point. and water are formed. C propanol D A propene 1, 2 and 3 B 1 and 2 only 37 X, Y and Z are three hydrocarbons. C 1 and 3 only D 2 and 3 only 15 2017 NOV P23 Q36 Y CH Z X naphtha CH2=CH 2reaction 3–CH=CH 2 petroleum. 36 Fuel oil and two fractions obtained from 38 The diagram shows aare sequence. CH3–CH2–CH=CH2 What are do compounds X, Z have in common? What the major uses these fractions? X Yofand Y butane ethene ethanol 1 They are all alkenes. fuel oil naphtha 2 They are all part of the same homologous series. Which the processes X, Ychemicals and Z? A row names jet fuel making 3 They all have the same boiling point. B jet fuel making roads X Y Z A C 1, 2 andship 3 fuelB 1 and 2 onlychemicals C 1 and 3 only D making A cracking fermentation respiration D ship fuel making roads B diagram cracking hydration 38 The shows a reaction sequence. combustion Z carbon dioxide and water abul fazal C distillation D distillation butane X fermentation hydration ethene respiration Y combustion ethanol 2 and 3 only Z carbon dioxide and water Which pair row of names the processes X, Y and Z? 39 Which compounds can be used to prepare CH3CH2COOCH2CH3? A ethanoic acid X and ethanol Y B ethanoic acid and propanol cracking fermentation © UCLESA 2017 Z respiration 0620/23/O/N/17 C B propanoic acid and ethanol cracking hydration combustion D C propanoic acid and propanol distillation fermentation respiration D distillation © UCLES 2017 Fuels and Cracking WS 1 hydration combustion 0620/21/O/N/17 [Turn over Abul Fazal A calcium carbonate B calcium hydroxide C calcium oxide D calcium sulfate 55 16 2019 JUN P23 Q35 35 Which fuel could be gasoline? Is it obtained from petroleum? 13 yes no 34 Which row describes the conditions used in the manufacture of sulfuric acid by the Contact process? Is it used as Is it used as fuel for cars? fuel for cars? catalyst pressure temperature A iron B iron high no low C A vanadium(V) oxide B high D vanadium(V) oxide low yes high yes no low C D low high 17 2020 MAR P22 Q35 35 Petroleum is an important raw material that is 14 separated into useful products. 34 Propane reacts with chlorine. Which terms describe petroleum and the method used to separate it? Which row shows a condition required for this reaction and identifies the type of reaction? description separation method condition compound A © UCLES 2019 type of reaction cracking 0620/23/M/J/19 B A compound fractional distillation phosphoric acid catalyst addition C B mixtureacid catalyst phosphoric D C mixture light ultraviolet crackingsubstitution fractional distillation addition D ultraviolet light substitution 36 Which statements about propene are correct? 18 2021 MAR P22 Q35 abul fazal 35 The pie chart represents the composition natural gas. 1 Propene contains only singleofbonds. 2 Propene decolourises Which sector represents methane? bromine water. 3 4 A Propene is obtained by cracking. B C A Propene is a hydrocarbon. 1 and 4 B 2, 3 and 4 C D 2 and 4 only D 4 only 37 Which row describes the production of ethanol and its properties? can be made from glucose can be made from ethene is used as a fuel is used as a solvent A key B = yes 36 Which ethene and C statement describes the reaction between steam? = no reaction which produces ethane and hydrogen gas as products A D a cracking B an addition reaction which produces ethanol as the only product C an oxidation reaction which produces ethanoic acid as the only product Abul Fazal Fuels and Cracking WS 1 D a slow reaction producing ethanol and carbon dioxide © UCLES 2020 0620/22/F/M/20 [Turn over A C H2 B C C8H18 C CH4 H2 D CH4 C8H18 56 19 2021 NOV P23 Q35 35 What is the main constituent of natural gas? A hydrogen B carbon monoxide C methane D nitrogen 13 36 Which statement describes the members of a homologous series? 20 2019 MAR P22 Q36 36 The distillation petroleum is shown. A fractional compounds with theofsame physical properties 11 group compounds containing the same functional B refinery gas compounds containing thea same number and type of bonds 34 C Ammonium sulfate is used as fertiliser. D compounds obtainedand fromsulfuric the same It is made from ammonia acid.raw material gasoline fraction Which words complete gaps 1, 2 and 3? 37 The structures of two compounds are shown. paraffin fraction The ......1...... is made by the ......2...... process in which ......3...... is used as a catalyst. H H H H O O diesel oil 1 C C O C2 H H C3 C C lubricating fraction ammonia Contact iron H O petroleum H H H H B ammonia Haber vanadium(V) oxide Which statements about these compounds are correct? C sulfuric acid Contact vanadium(V) oxide 1 sulfuric They acid have the same molecular formula. bitumen D Haber iron A H Which fraction is thehave leastsimilar volatile? 2 They chemical properties. 35 A Which process is used to obtain lime from limestone? bitumen 3 They are structural isomers. abul fazal B A A C B diesel cracking 1 onlyoil B 1 and 2 gasoline fraction fractional distillation D C refinery gas neutralisation C 2 and 3 D 1 and 3 D thermal decomposition 37 Which statement about members of a homologous series is correct? 21 2019 NOV P21 Q36 Successive membersbydiffer by CHdistillation. 3. 36 A Petroleum is separated fractional 0620/23/O/N/21 © UCLES 2021 [Turn over B Successive members have a molecular mass that differs by 14. Which statement about the fractions produced is correct? C They have the same molecular formula. A Bottled gas for heating and cooking is obtained from the naphtha fraction. D They have identical physical properties. B Diesel oil is used as a fuel for jet aircraft. C Substances used toon make polishes obtained from the lubricating fraction. 38 Ethanol is manufactured a large scale are by fermentation. D The kerosene fraction contains many useful waxes. Which statement about fermentation is correct? A It is a continuous process. 37 Which products are obtained by the cracking of an alkane? B A renewable raw material is used. alkene hydrogen water C It is a very fast reaction. produced ispure. D A The ethanol B Cracking WS 1 Fuels and C Abul Fazal A Limestone combines with water to produce slaked lime. B Lime is obtained from limestone by oxidation. C 57 Lime is used in the desulfurisation of flue12 gases. Lime is sulfate used inisthe treatment of alkaline soil. 34 D Ammonium used as a fertiliser. 22 2019 NOV P22 Q36 It is made from ammonia and sulfuric acid. 36 Some fractions obtained from petroleum are listed. Which words complete gaps 1, 2 and 3? position collected The ......1...... is made by the ......2...... process fraction usein which ......3...... is used in theas a catalyst. fractionating column 1 2 3 1 gasoline waxes and polishes below refinery gas A ammonia Contact iron 2 bitumen making roads above kerosene B ammonia Haber vanadium(V) oxide 3 kerosene jet fuel below gasoline C sulfuric acid Contact vanadium(V) oxide 4 refinery gas heating and cooking above gasoline D sulfuric acid Haber iron Which rows are correct? 1, 3 andof4reaction occurs when lime is manufactured from limestone? 35 A Which type B A 2, 3 and 4 combustion C B 3 and 4 only neutralisation D C 4 only redox D thermal decomposition 37 Which products are obtained by the cracking of an alkane? 23 2019 NOV P23 Q36 36 Which statement alkene is correct? hydrogen water A A Bitumenis used as a fuel for ships. B B Coal, natural gas and oxygen are all fuels. C C Hydrogen of natural gas. is the main constituent D D Petroleum by fractional distillation. is separatedinto useful substances 14 14 37 Which products are obtained by the cracking of14 an alkane? 24 2021 JUN P22 Q38 38 The flow chart shows how petroleum may be turned into a plastic. The flow chart shows howpetroleum petroleummay maybe be turned into a plastic. 38 38The flow chart alkeneshows how hydrogen water turned into a plastic. process process process process process process process A process process 11 2 33 3 saturated unsaturated saturated unsaturated 1 22 petroleum saturated unsaturated hydrocarbon Bpetroleum hydrocarbon petroleum hydrocarbon hydrocarbon hydrocarbon hydrocarbon C What areare processes What processes1,1,22and and3? 3? What 1, 2 and D are processes 3? abul fazal process11 process process 1 A cracking © UCLESA2019 cracking A cracking B cracking B cracking B cracking C fractional distillation C fractional distillation C fractional distillation D fractional distillation D fractional distillation distillation D fractional process 22 process process 2 fractional distillation 0620/22/O/N/19 fractional distillation fractional distillation polymerisation polymerisation polymerisation cracking cracking cracking polymerisation polymerisation polymerisation © UCLES 2019 plastic plastic plastic process 3 3 process process 3 polymerisation polymerisation polymerisation fractional distillation fractional distillation fractional distillation polymerisation polymerisation polymerisation cracking cracking cracking 0620/23/O/N/19 [Turn over 39 The structure of a synthetic polymer is shown. 39 structure of of aa synthetic syntheticpolymer polymerisisshown. shown. 39 The The structure O O O O O O O O OO O OO OO N C N C C N C N C C NN C NN C C NN CC C CC NN C H H H H Abul Fazal Fuels and Cracking WS 1 HH HH HH HH The structure shows that it is a ......1...... . It is formed by ......2...... polymerisation. The structure structure shows shows that thatititisisaa......1...... ......1....... .ItItisisformed formedbyby......2...... ......2......polymerisation. polymerisation. Which words complete gaps 1 and 2? 58 Organic Chemistry WS 2 14 14 6 Petroleum is a source of many important chemicals. 14 JUNisP41 Q06 of many important chemicals. 61 2016 Petroleum a source 6 Petroleum a source of many important (a) Name is two industrial processes whichchemicals. must take place to produce alkenes from petroleum. (a) Name two industrial processes which must take place to produce alkenes from petroleum. (a) Name two industrial processes which must take place to produce alkenes from petroleum. .................................................................................................................................................... .................................................................................................................................................... Fractional distillation of crude oil and the cracking of alkanes .................................................................................................................................................... .............................................................................................................................................. [2] .............................................................................................................................................. [2] .............................................................................................................................................. [2] (b) Ethene, CH2=CH2, and propene, CH2=CHCH3, can both be converted into polymers. (b) Ethene, CH2=CH2, and propene, CH2=CHCH3, can both be converted into polymers. , and propene, takes CH2=CHCH , can ethene both beforms converted into polymers. (b) (i) Ethene, CH What type of2polymerisation place 3when a polymer? 2=CH (i) What type of polymerisation takes place when ethene forms a polymer? (i) What type of polymerisation takes place when ethene forms a polymer? ....................................................................................................................................... [1] Addition polymerisation ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) What is the empirical formula of the polymer formed from ethene? (ii) What is the empirical formula of the polymer formed from ethene? (ii) What is the empirical formula of the polymer formed from ethene? ....................................................................................................................................... [1] CH2 ....................................................................................................................................... [1] ....................................................................................................................................... [1] (iii) Propene has the structural formula CH2=CHCH3. (iii) Propene has the structural formula CH2=CHCH3. (iii) Draw Propene the structural formula CHmade twohas repeat units of the polymer from 2=CHCH 3. propene. Draw two repeat units of the polymer made from propene. Draw two repeat units of the polymer made from propene. [2] [2] [2] (c) Ethene will react with steam to form ethanol. (c) Ethene will react with steam to form ethanol. (c) Ethene Propenewill willreact reactwith withsteam steamtotoform formethanol. two isomers, both of which are alcohols. Propene will react with steam to form two isomers, both of which are alcohols. Propene will structures react with steam toalcohols. form two isomers, both of which are alcohols. Suggest the of these Suggest the structures of these alcohols. Suggest the structures of these alcohols. abul fazal [2] [2] [2] © UCLES 2016 0620/41/M/J/16 © UCLES 2016 0620/41/M/J/16 © UCLESChemistry 2016 Organic WS 2 0620/41/M/J/16 Abul Fazal 1559 (d) Esters are organic chemicals noted for their characteristic smells. Ethanoic acid and methanol will react to form an ester. (i) Name the catalyst needed to form an ester from ethanoic acid and methanol. Sulfuric acid ....................................................................................................................................... [1] (ii) Name the ester formed when ethanoic acid reacts with methanol. methyl ethanoate ....................................................................................................................................... [1] (iii) Draw the structure of the ester formed when ethanoic acid reacts with methanol. Show all bonds. [2] (iv) Give the name of a polyester. PET ....................................................................................................................................... [1] [Total: 13] abul fazal Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at www.cie.org.uk after the live examination series. Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2016 Abul Fazal 0620/41/M/J/16 Organic Chemistry WS 2 60 7 2 2016 JUN P42 Q05 5 (a) Hydrocarbons are compounds which contain hydrogen and carbon only. • 10 cm3 of a gaseous hydrocarbon, CxHy, are burned in 100 cm3 of oxygen, which is an excess of oxygen. • After cooling to room temperature and pressure, there is 25 cm3 of unreacted oxygen, 50 cm3 of carbon dioxide and some liquid water. All volumes are measured under the same conditions of temperature and pressure. (i) What is meant by an excess of oxygen? More oxygen than what is needed for the reaction to take place ....................................................................................................................................... [1] (ii) What was the volume of oxygen that reacted with the hydrocarbon? 75 cm^3 ....................................................................................................................................... [1] (iii) Complete the table below to express the smallest whole number ratio of smallest whole number ratio of volumes volume of carbon dioxide produced volume of : hydrocarbon reacted volume of oxygen reacted volume of hydrocarbon reacted volume of oxygen reacted volume of carbon dioxide produced 2 15 10 : [1] (iv) Use your answer to (a)(iii) to find the mole ratio in the equation below. Complete the equation and deduce the formula of the hydrocarbon. abul fazal 2 10 10 15 .........C xHy(g) + .........O2(g) → .........CO2(g) + .........H2O(l) C5H10 formula of hydrocarbon = ........................................... [2] © UCLES 2016 Organic Chemistry WS 2 0620/42/M/J/16 [Turn over Abul Fazal 8 861 (b) Cracking is used to convert long chain alkanes into shorter chain alkanes and alkenes. Alkenes are unsaturated (b) Cracking is usedcompounds. to convert long chain alkanes into shorter chain alkanes and alkenes. Alkenes are unsaturated compounds. Decane, C10H22, can be cracked to give propene and one other product. Decane, C10H22, can be cracked to give propene and one other product. (i) Complete the chemical equation. (i) Complete the chemical equation. C10H22 → C3H6 + ............... [1] C7H16 C10H22 → C3H6 + ............... [1] (ii) What is meant by the term unsaturated? (ii) What is meant by the term unsaturated? ....................................................................................................................................... [1] A hydrocarbon that doesn't have all single bonds in its formula (displayed) ....................................................................................................................................... [1] (iii) Describe a test to show that propene is an unsaturated compound. (iii) Describe a test to show that propene is an unsaturated compound. test ...................................................................................................................................... bromine water test ...................................................................................................................................... result ................................................................................................................................... Turns water from brown to colourless [2] result ................................................................................................................................... [2] (c) Propene can be polymerised. The only product is polypropene. The equation for the is: polymerised. The only product is polypropene. The equation for the (c) polymerisation Propene can be polymerisation is: CH3 H CH3 H C C nC3H6 C C nC3H6 H H n H H n (i) Name the type of polymerisation that occurs. (i) Name the type Addition of polymerisation that occurs. polymerisation ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Deduce the maximum mass of polypropene that could be produced from 1 kg of propene. (ii) Deduce the maximum mass of polypropene that could be produced from 1 kg of propene. abul fazal (iii) (iii) 1 ............... kg [1] ............... kg [1] Give the empirical formula of Give the empirical formula of CH2 propene, ............................................................................................................................. propene, ............................................................................................................................. CH2 polypropene. ....................................................................................................................... [2] polypropene. ....................................................................................................................... [2] [Total: 13] [Total: 13] © UCLES 2016 0620/42/M/J/16 © UCLES 2016 0620/42/M/J/16 Abul Fazal Organic Chemistry WS 2 462 4 4 2 The structures of six organic compounds are shown. JUN P43 Q02 23 2016 The structures of six organic compounds are shown. B 2 The structures A of six organic compounds are shown. A B HB H H H AH H H H H H H H H C H H H C H C H C H H C C H C C C C H C C H H C C C H C H C H C H H H H H H H H H D E D E H HDH E H H H H C H H H H H C H C HH C H H H C C H HH C H H C H H H C O H H C H C C H O H H C C C H O H H H C H C C H H H H H H H H (a) Give the name of F. H H H H H H H H H H H H C C C H H H C C HC O H O H C O C C C C C O H O H O H F F H F H H H H C H C C C C H C H H H H H H H H H H H C C C H H H H H H (a) Give the name of F. (a) Give the name of F. .............................................................................................................................................. [1] .............................................................................................................................................. [1] Butane .............................................................................................................................................. [1] (b) Identify two of the compounds that are members of the same homologous series. (b) Give Identify of theformula compounds are members of the same homologous series. thetwo general of thisthat homologous series. (b) Give Identify of theformula compounds are members of the same homologous series. thetwo general of thisthat homologous series. Give the general formula of this homologous series. compounds ................................................................................................................................ A and B compounds ................................................................................................................................ compounds ................................................................................................................................ general formula .......................................................................................................................... CnH2n general formula .......................................................................................................................... [2] general formula .......................................................................................................................... [2] [2] (c) Which two compounds are isomers of each other? (c) Explain Which two are isomers of each other? whycompounds they are isomers. (c) Explain Which two are isomers of each other? whycompounds they are isomers. Explain why ................................................................................................................................ they are isomers. compounds E and F compounds ................................................................................................................................ compounds ................................................................................................................................ explanation They have different structures. E is methyl propane and F is explanation ................................................................................................................................ explanation ................................................................................................................................ .................................................................................................................................................... Butane .................................................................................................................................................... [3] .................................................................................................................................................... [3] [3] (d) Explain why B is an unsaturated hydrocarbon. (d) Explain why B is an unsaturated hydrocarbon. It only consists single bonds (d) Explain why B is anofunsaturated hydrocarbon. .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .............................................................................................................................................. [2] 5 .............................................................................................................................................. [2] .............................................................................................................................................. [2] (e) Describe how D is manufactured from B. Give a chemical equation for the reaction. abul fazal D is an alcohol. B is an alkene. When an alkene, in this case, ethene, reacts with water .................................................................................................................................................... © UCLES 2016 0620/43/M/J/16 an alcohol, ethanol is formed. Its equation is C2H4 + H20 ---> C2H5OH. This reaction .................................................................................................................................................... © UCLES 2016 0620/43/M/J/16 © UCLES 2016 0620/43/M/J/16 takes place at a temperature of 570 degrees and at 60 - 70 atm with acid catalyst .............................................................................................................................................. [3] Organic WS (f) Chemistry Compound A2 forms an addition polymer. Draw two repeat units of the addition polymer formed from A. Abul Fazal .................................................................................................................................................... .............................................................................................................................................. [3] 63 (f) Compound A forms an addition polymer. Draw two repeat units of the addition polymer formed from A. [2] 4 2016 MAR P42 Q07 7 12 [Total: 13] (a) Alkanes and alkenes are examples of hydrocarbons. (i) What is meant by the term hydrocarbon? A compound that only contains hydrogen and carbon. ............................................................................................................................................. ....................................................................................................................................... [1] (ii) Give the general formula of straight-chain CnH2n+2 alkanes, .............................................................................................................................. CnH2n alkenes. .............................................................................................................................. [2] (b) A compound X contains carbon, hydrogen and oxygen only. abul fazal X contains 54.54% of carbon by mass, 9.09% of hydrogen by mass and 36.37% of oxygen by mass. (i) © UCLES 2016 Calculate the empirical formula of compound X. 0620/43/M/J/16 [Turn over [2] (ii) Compound X has a relative molecular mass of 88. Deduce the molecular formula of compound X. Abul Fazal Organic Chemistry WS 2 alkenes. .............................................................................................................................. [2] 64 (b) A compound X contains carbon, hydrogen and oxygen only. X contains 54.54% of carbon by mass, 9.09% of hydrogen by mass and 36.37% of oxygen by mass. (i) Calculate the empirical formula of compound X. [2] (ii) Compound X has a relative molecular mass of 88. Deduce the molecular formula of compound X. 13 13 (c) An ester has the molecular formula C3H6O2. (c) An ester has the molecular formula C3H6O2. Name and give the structural formulae of two esters with the molecular formula C3H6O2. Name and give the structural formulae of two esters with the molecular formula C3H6O2. [2] abul fazal name of ester name of ester © UCLES 2016 structural formula structural formula 0620/42/F/M/16 [4] [4] (d) Name the ester produced from the reaction of propanoic acid and methanol. (d) Name the ester produced from the reaction of propanoic acid and methanol. methyl propanoate .............................................................................................................................................. [1] .............................................................................................................................................. [1] (e) A polyester is represented by the structure shown. (e) A polyester is represented by the structure shown. O O O O C O C C O C (i) (i) O O What type of polymerisation is used for the production of polyesters? What type of polymerisation is used for the production of polyesters? ....................................................................................................................................... [1] Organic Chemistry WS 2 Abul ....................................................................................................................................... [1]Fazal (ii) Which simple molecule is removed when the polyester is formed? (ii) Which simple molecule is removed when the polyester is formed? 65 4 4 NOV P41 35 2016 (a) Petroleum is Q03 a mixture of hydrocarbons. It is separated into useful fractions by fractional 3 (a) Petroleum is a can mixture of hydrocarbons. It is separated useful fractions by fractional distillation. This be done using the fractionating column into shown. distillation. This can be done using the fractionating column shown. K K L L M M petroleum petroleum X X N N O O P P (i) (i) (ii) (ii) What happens to the petroleum at point X, before it enters the fractionating column? What happens to the petroleum at point X, before it enters the fractionating column? ............................................................................................................................................. The crude oil that needs to be distilled is heated and it becomes a gas at X. ............................................................................................................................................. ....................................................................................................................................... [1] ....................................................................................................................................... [1] State two ways in which fraction O differs from fraction L. State two ways in which fraction O differs from fraction L. ............................................................................................................................................. Fraction O is more viscous than Fraction L ............................................................................................................................................. ............................................................................................................................................. Fraction O has lower flammability and volatility than Fraction L. ............................................................................................................................................. ....................................................................................................................................... [2] ....................................................................................................................................... [2] abul fazal (b) Most of the hydrocarbons obtained from petroleum are alkanes. The alkanes are an (b) Most of the series hydrocarbons obtained from petroleum are alkanes. The alkanes are an homologous of saturated hydrocarbons with the general formula C nH2n+2. homologous series of saturated hydrocarbons with the general formula CnH2n+2. Give two characteristics, other than having the same general formula, of members of an Give two characteristics, other than having the same general formula, of members of an homologous series. homologous series. Their chain length of the successor in a homologous series increases by CH2 .................................................................................................................................................... .................................................................................................................................................... As chain length increases, melting and boiling points also increase. .................................................................................................................................................... .................................................................................................................................................... .............................................................................................................................................. [2] .............................................................................................................................................. [2] © UCLES 2016 0620/41/O/N/16 © UCLES 2016 0620/41/O/N/16 Abul Fazal Organic Chemistry WS 2 5 566 (c) The alkane with the molecular formula C5H12 can exist as a number of structural isomers. (c) The alkane with the molecular formula C5H12 can exist as a number of structural isomers. Draw the structures of two isomers with the formula C5H12. Draw the structures of two isomers with the formula C5H12. [2] [2] (d) The alkane ethane has the structure shown. (d) The alkane ethane has the structure shown. H H H H H C C H H C C H H H H H When a mixture of ethane and chlorine is exposed to ultraviolet light a substitution reaction takes When place. a mixture of ethane and chlorine is exposed to ultraviolet light a substitution reaction takes place. Draw the structure of one organic product from this substitution reaction. Draw the structure of one organic product from this substitution reaction. [1] [1] 6 abul fazal (e) Isoprene is a naturally occurring hydrocarbon. (i) Explain how the name of isoprene suggests that it contains a C=C double bond. Anything ending with an ene is in the alkenes, hence it must have a double bond [1] ....................................................................................................................................... (ii) A sample of isoprene had the following composition by mass: C, 88.24%; H, 11.76%. Calculate the empirical formula of isoprene. Show all your working. 88.24 ÷ 12 and 11.76 ÷ 1 7.353 and 11.76 Therefore, 1 mole of C reacting with x moles of h ---> 1 mol and 11.76 ÷ 7.353 = 1.6 so, 5:8 is the ratio Therefore - C5H8 C5H8 empirical formula = .............................. [3] (iii) © UCLES 2016 © UCLES 2016 What additional information would be required to calculate the molecular formula of isoprene? [Turn over 0620/41/O/N/16 The relative molecular mass of isoprene ....................................................................................................................................... [1] [Turn over 0620/41/O/N/16 [Total: 13] 4 (a)Chemistry Ammonia,WS NH23, is made by reacting nitrogen with hydrogen in the Haber process. Organic (i) Write a chemical equation for the formation of ammonia in the Haber process. Abul Fazal 67 8 8 6 2016 NOV P42 Q05 (c) When one mole of bromine, Br2, reacts with one mole of propene, one organic product is (c) formed. When one mole of bromine, Br2, reacts with one mole of propene, one organic product is formed. (i) Which part of the propene molecule reacts with bromine? (i) Which part of the propene molecule reacts with bromine? ....................................................................................................................................... [1] The double bond ....................................................................................................................................... [1] (ii) What is the name of the type of reaction which takes place between bromine and propene? (ii) What is the name of the type of reaction which takes place between bromine and propene? ....................................................................................................................................... [1] Addition reaction ....................................................................................................................................... [1] (d) When one mole of chlorine, Cl 2, reacts with one mole of propane, a mixture of two structural (d) isomers When one mole of chlorine, Cl 2, reacts with one mole of propane, a mixture of two structural is formed. isomers is formed. (i) What is the name of the type of reaction which takes place between chlorine and propane? (i) What is the name of the type of reaction which takes place between chlorine and propane? Substitution reaction ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Explain what is meant by the term structural isomers. (ii) Explain what is meant by the term structural isomers. Compounds that have the same molecular formula but different structural formula ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... [2] ....................................................................................................................................... [2] (iii) Draw the structure of two structural isomers formed when one mole of chlorine reacts with (iii) Draw the structure of two structural isomers formed when one mole of chlorine reacts with one mole of propane. one mole of propane. abul fazal © UCLES 2016 © UCLES 2016 Abul Fazal [2] [2] 0620/42/O/N/16 0620/42/O/N/16 Organic Chemistry WS 2 12 1268 6 The alkenes and alkanes are both examples of 12homologous series which are hydrocarbons. 6 The alkenes and alkanes are both examples of 12homologous series which are hydrocarbons. JUNis P41 (a) meant by the are termboth hydrocarbon? 67 2017 The What alkenes and Q06 alkanes examples of homologous series which are hydrocarbons. is meant by the are termboth hydrocarbon? 6 (a) The What alkenes and alkanes examples of homologous series which are hydrocarbons. .................................................................................................................................................... (a) What is meant by the term hydrocarbon? .................................................................................................................................................... (a) What is meant by the term hydrocarbon? .............................................................................................................................................. [2] .................................................................................................................................................... A compound that only contains hydrogen and carbon .............................................................................................................................................. [2] .................................................................................................................................................... .............................................................................................................................................. [2] (b) Give three characteristics of an homologous series. .............................................................................................................................................. [2] (b) Give three characteristics of an homologous series. ................................................................................................................................................. (b) 1 Give three characteristics of an homologous series. ................................................................................................................................................. (b) 1 Give three characteristics of an homologous series. Chain length increases by CH2 each time 2 ................................................................................................................................................. 1 ................................................................................................................................................. 2 ................................................................................................................................................. 1 They have the same functional group 3 2 ................................................................................................................................................. ................................................................................................................................................. 3 [3] 2 ................................................................................................................................................. [3] They fit in the same general formula 3 ................................................................................................................................................. 3 ................................................................................................................................................. [3] (c) Name and draw the structure of the second member of the alkene homologous series. [3] (c) Show Name all and the structure of the the bonds. second member of the alkene homologous series. ofdraw the atoms and all of ofdraw the atoms and all of (c) Show Name all and the structure of the the bonds. second member of the alkene homologous series. name .......................................................................................................................................... (c) Show Name all and the structure of the the bonds. second member of the alkene homologous series. ofdraw the atoms and all of Propene name .......................................................................................................................................... Show all of the atoms and all of the bonds. structure name .......................................................................................................................................... structure name .......................................................................................................................................... structure structure [2] [2] [2] [2] (d) Alcohols can be made from alkenes. (d) Alcohols can be made from alkenes. thecan reagent and from conditions needed to convert an alkene into an alcohol. (d) Name Alcohols be made alkenes. thecan reagent and from conditions needed to convert an alkene into an alcohol. (d) Name Alcohols be made alkenes. You add water to the alkene, and it reacts with it at 570 degrees Celsius at 60 - 70 atm .................................................................................................................................................... Name the reagent and conditions needed to convert an alkene into an alcohol. .................................................................................................................................................... Name the reagent and conditions needed to convert an alkene into an alcohol. with phosphoric acid acting as catalyst .............................................................................................................................................. [2] .................................................................................................................................................... .............................................................................................................................................. [2] .................................................................................................................................................... .............................................................................................................................................. [2] .............................................................................................................................................. [2] abul fazal © UCLES 2017 0620/41/M/J/17 © UCLES 2017 0620/41/M/J/17 © UCLES 2017 0620/41/M/J/17 © UCLES 2017 0620/41/M/J/17 Organic Chemistry WS 2 Abul Fazal 13 1369 (e) The alcohol butanol, CH3CH2CH2CH2OH, can be converted into a carboxylic acid with four carbon atoms. (e) The alcohol butanol, CH3CH2CH2CH2OH, can be converted into a carboxylic acid with four carbon atoms. (i) Name the carboxylic acid formed from butanol and draw its structure. Show all of the all of the bonds. (i) atoms Name and the carboxylic acid formed from butanol and draw its structure. Show all of the atoms and all of the bonds. name ................................................................................................................................... Butanoic acid name ................................................................................................................................... structure structure (ii) (ii) (iii) (iii) [2] [2] Ethanoic acid can be formed from ethanol by fermentation. It can also be formed by the addition a suitable reagent. Ethanoicofacid can bechemical formed from ethanol by fermentation. It can also be formed by the addition of a suitable chemical reagent. Name the reagent needed to convert ethanol into ethanoic acid. Name the reagent needed to convert ethanol into ethanoic acid. ....................................................................................................................................... [2] Acidified Potassium manganate(VII) ....................................................................................................................................... [2] State the type of chemical change which occurs when ethanol is converted into ethanoic State theacid. type of chemical change which occurs when ethanol is converted into ethanoic acid. ....................................................................................................................................... [1] Oxidation ....................................................................................................................................... [1] (f) Describe how a student could prepare the ester methyl ethanoate in a school laboratory. your description give could prepare the ester methyl ethanoate in a school laboratory. (f) In Describe how a student In your description give ● the names of the two starting organic chemicals, ● the essential needed, names of reaction the two conditions starting organic chemicals, ● the a chemical equation the reaction. essential reactionfor conditions needed, ● a chemical equation for the reaction. 1) Methanol and ethanoic acid .................................................................................................................................................... .................................................................................................................................................... 2) Sulfuric acid catalyst .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .............................................................................................................................................. [5] .............................................................................................................................................. [5] [Total: 19] [Total: 19] abul fazal © UCLES 2017 0620/41/M/J/17 © UCLES 2017 0620/41/M/J/17 Abul Fazal [Turn over [Turn over Organic Chemistry WS 2 70 12 12 P42 Q06 68 2017 (a) AnJUN homologous series is a ‘family’ of organic compounds whose names have the same ending. 6 (a) An homologous series is a ‘family’ of organic compounds whose names have the same ending. (i) Name the homologous series for which the names of the organic compounds end in -ene -oic acid. (i) and Name the homologous series for which the names of the organic compounds end in -ene and -oic acid. -ene .............................................................................................................................. [1] Alkenes -ene .............................................................................................................................. [1] -oic acid ........................................................................................................................ [1] Carboxylic acids -oic acid ........................................................................................................................ [1] (ii) State two characteristics of an homologous series. (ii) State two characteristics of an homologous series. ............................................................................................................................................. Melting point and boiling point increase with chain length ............................................................................................................................................. ....................................................................................................................................... [2] The have the same functional group ....................................................................................................................................... [2] (b) Propan-1-ol is a member of the homologous series of alcohols. It reacts in the same way as ) andofwith carboxylic acids. with is acidified potassium manganate(VII (b) ethanol Propan-1-ol a member of the homologous series alcohols. It reacts in the same way as ethanol with acidified potassium manganate(VII) and with carboxylic acids. Name the type of compound that is formed when propan-1-ol is heated with Name the type of compound that is formed when propan-1-ol is heated with acidified potassium manganate(VII), ........................................................................................ acidified potassium manganate(VII), ........................................................................................ ethanoic acid and a suitable catalyst. ........................................................................................ [2] 13 ethanoic acid and a suitable catalyst. ........................................................................................ [2] (c) The structure of prop-2-enoic (acrylic) acid is shown. (i) H CO2H C C H H What would you see if prop-2-enoic acid were added to aqueous bromine, ............................................................................................................... abul fazal a solution of sodium carbonate. .......................................................................................... [2] (ii) Prop-2-enoic acid can be polymerised to form poly(acrylic acid). Suggest the type of polymerisation that occurs and draw one repeat unit of the polymer. type of polymerisation ......................................................................................................... repeat unit © UCLES 2017 0620/42/M/J/17 © UCLES 2017 0620/42/M/J/17 Organic Chemistry WS 2 [3] [Total: 11] Abul Fazal 71 3 9 2017 JUN P43 Q02 2 Cyclopropane is a colourless gas. Cyclopropane reacts with bromine at room temperature. The chemical equation for the reaction is shown. H H C C H H C H Br Br Br H cyclopropane (a) (i) + bromine H H H C C C H H H Br dibromopropane What is the empirical formula of cyclopropane? ....................................................................................................................................... [1] (ii) What colour change, if any, would you see when cyclopropane is bubbled into aqueous bromine? initial colour ......................................................................................................................... final colour .......................................................................................................................... [2] (b) The reaction of cyclopropane with bromine is exothermic. (i) Complete the energy level diagram for this reaction by ● ● adding the product of the reaction, labelling the energy change, ∆H. abul fazal energy cyclopropane + bromine [2] © UCLES 2017 Abul Fazal 0620/43/M/J/17 [Turn over Organic Chemistry WS 2 72 7 7 10 JUN P43 as Q04 4 2017 Gasoline is used a fuel for cars. It is a mixture of hydrocarbons. 4 Gasoline is used as a fuel for cars. It is a mixture of hydrocarbons. (a) Name the raw material from which gasoline is obtained. (a) Name the raw material from which gasoline is obtained. .............................................................................................................................................. [1] .............................................................................................................................................. [1] (b) One of the compounds in gasoline is heptane, C7H16. Heptane is a saturated hydrocarbon. (b) One of the compounds in gasoline is heptane, C7H16. Heptane is a saturated hydrocarbon. (i) What is meant by the term saturated hydrocarbon? (i) What is meant by the term saturated hydrocarbon? saturated ............................................................................................................................. saturated ............................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. hydrocarbon ........................................................................................................................ hydrocarbon ........................................................................................................................ ............................................................................................................................................. [3] ............................................................................................................................................. [3] (ii) To which homologous series does heptane belong? (ii) To which homologous series does heptane belong? ....................................................................................................................................... [1] ....................................................................................................................................... [1] (iii) Give two characteristics of an homologous series. (iii) Give two characteristics of an homologous series. 1 .......................................................................................................................................... 1 .......................................................................................................................................... 2 .......................................................................................................................................... [2] 2 .......................................................................................................................................... [2] (iv) Complete the chemical equation for the complete combustion of heptane. (iv) Complete the chemical equation for the complete combustion of heptane. ....................... + ....................... C7H16 + ..........O2 [2] ....................... + ....................... C7H16 + ..........O2 [2] abul fazal © UCLES 2017 0620/43/M/J/17 © UCLES 2017 0620/43/M/J/17 Organic Chemistry WS 2 [Turn over [Turn over Abul Fazal 973 (d) The formula C4H10 represents two structural isomers, A and B. H H H H H H C C C C H H H H H H H H C H H C C C H H H A (i) H B Name isomer A. ....................................................................................................................................... [1] (ii) What is meant by the term structural isomers? ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... [2] (iii) Isomer B reacts with chlorine in a substitution reaction. Give the conditions required for the reaction to occur and draw the structures of two possible products, one of which is organic and one of which is not organic. conditions ........................................................................................................................... structures of products abul fazal [3] [Total: 23] © UCLES 2017 Abul Fazal 0620/43/M/J/17 [Turn over Organic Chemistry WS 2 74 2 11 2017 MAR P42 Q01 1 (a) Five organic compounds have the following structures. A H B H H H H C C C C H H H H H H C H H H H C C C C H H H (i) H H H C C C C H H H D Br H H E H H C C H H Br Br H H H C C C H H H Br Which compound is butane? ....................................................................................................................................... [1] (ii) Which two compounds are structural isomers of each other? ....................................................................................................................................... [1] (iii) Which compound can be made by reacting an alkene with bromine? ....................................................................................................................................... [1] (iv) Which compound is a saturated hydrocarbon? ....................................................................................................................................... [1] (v) Which compound has the empirical formula C2H5? abul fazal ....................................................................................................................................... [1] (vi) Name the two products made during the complete combustion of compound C. ....................................................................................................................................... [1] © UCLES 2017 Organic Chemistry WS 2 0620/42/F/M/17 Abul Fazal 375 (b) Petroleum can be separated into useful substances using the apparatus shown. refinery gas gasoline fraction naphtha fraction X diesel oil fraction fuel oil fraction Y petroleum lubricating fraction and bitumen (i) Name the fraction which is the most viscous. ....................................................................................................................................... [1] (ii) Name the fraction with the smallest molecules. ....................................................................................................................................... [1] (iii) Name the fraction which has the weakest attractive forces between molecules. ....................................................................................................................................... [1] (iv) Fraction X is used as jet fuel. Name fraction X. abul fazal ....................................................................................................................................... [1] (v) What happens at point Y on the diagram? ....................................................................................................................................... [1] 6 12 2017 NOV P41 Q04 4 [Total: 11] (a) Ethanol, C2H5OH, can be made by fermentation. (i) Complete the chemical equation for the formation of ethanol by fermentation. C6H12O6 (ii) ......C2H5OH + .............................. [2] State two conditions required for fermentation. 1 .......................................................................................................................................... © UCLES 2017 2 .......................................................................................................................................... [2] [Turn over 0620/42/F/M/17 (b) Ethanol can also be made by the catalytic hydration of ethene. The equation for the reaction is shown. Abul Fazal (i) C2H4 + H2O Name a suitable catalyst for this reaction. C2H5OH Organic Chemistry WS 2 1 .......................................................................................................................................... 2 .......................................................................................................................................... 76 [2] (b) Ethanol can also be made by the catalytic hydration of ethene. The equation for the reaction is shown. C2H4 + H2O (i) C2H5OH Name a suitable catalyst for this reaction. ....................................................................................................................................... [1] (ii) Calculate the maximum mass of ethanol that can be made from 56 g of ethene. maximum mass of ethanol = ............................. g [2] (c) Ethanol can be oxidised to form ethanoic acid. (i) Name a suitable oxidising agent for this reaction. 7 [1] ....................................................................................................................................... (ii) A molecule of ethanoic acid has the structure shown. H H C H O C O H Complete the dot-and-cross diagram to show the electron arrangement in ethanoic acid. Show outer shell electrons only. abul fazal H H © UCLES 2017 C O C 0620/41/O/N/17 H O H [3] (d) Ethanoic acid is a weak acid. (i) When referring to an acid, what is meant by the term weak? ............................................................................................................................................. ....................................................................................................................................... [1] (ii) Describe how you could show that ethanoic acid is a weaker acid than hydrochloric acid. Organic Chemistry WS 2 Abul Fazal ............................................................................................................................................. ............................................................................................................................................. [3] 77 (d) Ethanoic acid is a weak acid. (i) When referring to an acid, what is meant by the term weak? ............................................................................................................................................. ....................................................................................................................................... [1] (ii) Describe how you could show that ethanoic acid is a weaker acid than hydrochloric acid. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... [3] 8 (e) Carboxylic acids react with alcohols to make esters. The structure of an ester is shown. H H H C C H H O C O H H H H C C C C H H H H H [Turn over 0620/41/O/N/17 Draw the structures of the carboxylic acid and alcohol from which this ester can be made. Give the names of the carboxylic acid and alcohol. © UCLES 2017 structure of the carboxylic acid abul fazal name of the carboxylic acid ....................................................................................................... structure of the alcohol name of the alcohol ................................................................................................................... [4] [Total: 19] Abul Fazal Organic Chemistry WS 2 78 13 2017 NOV P42 Q03 7 (d) Dodecane is an alkane containing 12 carbon atoms. Ethanol can be manufactured from dodecane in a two-stage process. In stage 1, each molecule of dodecane is converted into three molecules of ethene and one molecule of another hydrocarbon. (i) Name the process which occurs in stage 1. ....................................................................................................................................... [1] (ii) Write a chemical equation for the reaction which occurs in stage 1. ....................................................................................................................................... [2] In stage 2, ethene reacts with steam to produce ethanol. (iii) State two conditions needed for stage 2. 1 .......................................................................................................................................... 2 .......................................................................................................................................... [2] (iv) Name the type of reaction which occurs in stage 2. ....................................................................................................................................... [1] (v) Suggest how to test the purity of the ethanol produced. ............................................................................................................................................. ....................................................................................................................................... [2] abul fazal © UCLES 2017 Organic Chemistry WS 2 0620/42/O/N/17 [Turn over Abul Fazal 879 (e) Ethanol can also be manufactured by the fermentation of glucose, C6H12O6. (i) State two conditions needed for the fermentation of glucose. 1 .......................................................................................................................................... 2 .......................................................................................................................................... [2] (ii) Complete the chemical equation for the fermentation of glucose. C6H12O6 (iii) ......C2H5OH + .............................. [2] One disadvantage of fermentation is that the maximum concentration of ethanol produced is about 15%. Suggest why the concentration of ethanol produced by fermentation does not exceed 15%. ............................................................................................................................................. ....................................................................................................................................... [1] (iv) Give one other disadvantage of manufacturing ethanol by fermentation. ....................................................................................................................................... [1] (v) Give one advantage, other than cost, of manufacturing ethanol by fermentation. ....................................................................................................................................... [1] (vi) Suggest the name of a process to obtain ethanol from a mixture of ethanol and water. ....................................................................................................................................... [1] abul fazal © UCLES 2017 Abul Fazal 0620/42/O/N/17 Organic Chemistry WS 2 80 9 14 2017 NOV P43 Q06 6 (a) Alkanes and alkenes are two homologous series of hydrocarbons. (i) What is meant by the term hydrocarbon? ....................................................................................................................................... [1] (ii) What is the general formula of the homologous series of alkanes, .............................................................................................................................. alkenes? ............................................................................................................................. [2] (iii) Other than having a general formula, state two characteristics of a homologous series. 1 .......................................................................................................................................... 2 .......................................................................................................................................... [2] (iv) The structure of an alkene molecule with the molecular formula C4H8 is shown. H H H H C C C C H H H H Draw the structure of a different alkene molecule with the molecular formula C4H8. Show all of the atoms and all of the bonds. (v) abul fazal [1] What term describes molecules with the same molecular formula but different structural formulae? ....................................................................................................................................... [1] © UCLES 2017 Organic Chemistry WS 2 0620/43/O/N/17 [Turn over Abul Fazal 81 10 (b) 25 cm3 of a gaseous hydrocarbon, CxHy, were burnt in 150 cm3 of oxygen. This was an excess of oxygen. After cooling, the volume of the gases remaining was 100 cm3. This consisted of 75 cm3 of carbon dioxide and 25 cm3 of unreacted oxygen. The water that was produced in the reaction was liquid. All volumes were measured at the same temperature and pressure. (i) What is meant by an excess of oxygen? ....................................................................................................................................... [1] (ii) What was the volume of oxygen that reacted with the hydrocarbon? ............................. cm3 [1] (iii) Complete the table to show the smallest whole number ratio of volumes. volume of hydrocarbon reacted smallest whole number ratio of volumes : volume of oxygen reacted : : volume of carbon dioxide produced : [1] (iv) Use your answer to (b)(iii) to balance the chemical equation. Deduce the formula of the hydrocarbon. CxHy(g) + ......O2(g) ......CO2(g) + ......H2O(l) abul fazal formula of the hydrocarbon = ............................. [2] © UCLES 2017 Abul Fazal [Total: 12] 0620/43/O/N/17 Organic Chemistry WS 2 82 8 8 15 JUN P42 Q07 7 2018 Many organic compounds, such as alcohols, carboxylic acids and esters, contain the elements hydrogen and oxygen only. 7 carbon, Many organic compounds, such as alcohols, carboxylic acids and esters, contain the elements carbon, hydrogen and oxygen only. (a) Compound R has the following composition by mass: C, 60.00%; H, 13.33%; O, 26.67%. (a) Compound R has the following composition by mass: C, 60.00%; H, 13.33%; O, 26.67%. Calculate the empirical formula of compound R. Calculate the empirical formula of compound R. empirical formula = .............................. [2] empirical formula = .............................. [2] (b) Compound S has the empirical formula C2H4O and a relative molecular mass of 88. (b) Compound S has the empirical formula C2H4O and a relative molecular mass of 88. Calculate the molecular formula of compound S. Calculate the molecular formula of compound S. molecular formula = .............................. [2] molecular formula = .............................. [2] abul fazal © UCLES 2018 0620/42/M/J/18 © UCLES 2018 0620/42/M/J/18 Organic Chemistry WS 2 Abul Fazal 9 983 (c) Compounds T and V both have the molecular formula C3H6O2. (c) Compounds T and V both have the molecular formula C3H6O2. ● Compound T produces bubbles of carbon dioxide gas when it is added to aqueous ● Compound T produces bubbles of carbon dioxide gas when it is added to aqueous sodium carbonate. sodium carbonate. ● Compound V is an ester. ● Compound V is an ester. (i) What is the name given to compounds with the same molecular formula but different (i) structures? What is the name given to compounds with the same molecular formula but different structures? ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Draw the structures of compounds T and V. Show all of the atoms and all of the bonds. (ii) Draw the structures of compounds T and V. Show all of the atoms and all of the bonds. compound T compound T compound V compound V (iii) (iii) [2] [2] All compounds with the molecular formula C3H6O2 can undergo complete combustion in All excess compounds with the molecular formula C3H6O2 can undergo complete combustion in an of oxygen. an excess of oxygen. Complete the chemical equation for this reaction. Complete the chemical equation for this reaction. ........................ + ........................ C3H6O2 + ........................ ........................ + ........................ C3H6O2 + ........................ [2] [2] abul fazal (d) Compound W has the molecular formula C2H6O. Compound W reacts when heated with (d) ethanoic Compound Wand hasa the molecular formula C2H6O. Compound acid catalyst to produce a sweet-smelling liquid. W reacts when heated with ethanoic acid and a catalyst to produce a sweet-smelling liquid. (i) Give the name of the homologous series to which compound W belongs. (i) Give the name of the homologous series to which compound W belongs. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Draw the structure of compound W. Show all of the atoms and all of the bonds. (ii) Draw the structure of compound W. Show all of the atoms and all of the bonds. [1] [1] © UCLES 2018 0620/42/M/J/18 © UCLES 2018 0620/42/M/J/18 Abul Fazal [Turn over [Turn over Organic Chemistry WS 2 10 1084 (e) Alkanes and alkenes are hydrocarbons. (e) Alkanes and alkenes are hydrocarbons. (i) What is meant by the term hydrocarbon? (i) What is meant by the term hydrocarbon? ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... [2] ....................................................................................................................................... [2] (ii) State the general formula of: (ii) State the general formula of: alkanes ............................................................................................................................... alkanes ............................................................................................................................... alkenes ............................................................................................................................... alkenes ............................................................................................................................... [2] [2] (f) Ethanol can be produced from long-chain alkanes as shown. (f) Ethanol can be produced from long-chain alkanes as shown. step 1 step 2 long-chain alkane step 1 ethene step 2 ethanol ethene ethanol long-chain alkane Describe the two-stage manufacture of ethanol from the long-chain alkane octane, C8H18. Describe the two-stage manufacture of ethanol from the long-chain alkane octane, C8H18. Include: Include: ● the names of the types of chemical reactions that occur ● the names of the types of chemical reactions that occur reaction equations ● reaction equations conditions. ● reaction conditions. step 1 ........................................................................................................................................ step 1 ........................................................................................................................................ .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... step 2 ........................................................................................................................................ step 2 ........................................................................................................................................ .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .............................................................................................................................................. [5] .............................................................................................................................................. [5] [Total: 20] [Total: 20] abul fazal © UCLES 2018 © UCLES 2018 Organic Chemistry WS 2 0620/42/M/J/18 0620/42/M/J/18 Abul Fazal 85 7 16 2018 JUN P43 Q04 4 Ethanol is a member of the homologous series of alcohols. (a) Give two characteristics of members of a homologous series. 1 ................................................................................................................................................. 2 ................................................................................................................................................. [2] (b) The structure of ethanol is shown. H H H C C H H O H Complete the dot-and-cross diagram to show the electron arrangement in a molecule of ethanol. Show outer shell electrons only. H H H C C H H O H [2] (c) Ethanol can be produced by the catalytic addition of steam to ethene or by the fermentation of glucose. abul fazal (i) Write a chemical equation for the production of ethanol by the catalytic addition of steam to ethene. ....................................................................................................................................... [1] (ii) Write a chemical equation for the production of ethanol by the fermentation of glucose, C6H12O6. ....................................................................................................................................... [1] (iii) State one advantage of producing ethanol by the catalytic addition of steam to ethene. Your answer must not refer to cost. ....................................................................................................................................... [1] (iv) State one advantage of producing ethanol by the fermentation of glucose. Your answer must not refer to cost. ....................................................................................................................................... [1] © UCLES 2018 Abul Fazal 0620/43/M/J/18 [Turn over Organic Chemistry WS 2 86 8 8 (d) (d) Ethanol Ethanol can can be be oxidised oxidised to to ethanoic ethanoic acid. acid. State the the chemical chemical reagent reagent needed needed to to oxidise oxidise ethanol ethanol to to ethanoic ethanoic acid. acid. State .............................................................................................................................................. .............................................................................................................................................. [1] [1] (e) (e) Ethanoic Ethanoic acid acid reacts reacts with with ethanol ethanol in in the the presence presence of of an an acid acid catalyst. catalyst. The The products products are are an an organic compound compound and and water. water. organic (i) (i) Draw Draw the the structure structure of of the the organic organic compound compound formed. formed. Show Show all all of of the the atoms atoms and and all all of of the the bonds. bonds. [2] [2] (ii) (ii) State State the the name name of of the the organic organic compound compound formed. formed. ....................................................................................................................................... [1] [1] ....................................................................................................................................... (iii) (iii) Which Which homologous homologous series series does does the the organic organic compound compound formed formed belong belong to? to? ....................................................................................................................................... ....................................................................................................................................... [1] [1] (f) (f) Ethanoic Ethanoic acid, acid, CH CH33COOH, COOH, is is a a weak weak acid. acid. It It reacts reacts with with copper( copper(II II)) carbonate carbonate to to form form the the salt salt copper( II ) ethanoate, Cu(CH COO) . copper(II) ethanoate, Cu(CH33COO)22. (i) (i) What is is meant meant by by the the term term weak weak when when applied applied to to acids? acids? What ....................................................................................................................................... ....................................................................................................................................... [1] [1] (ii) (ii) Describe Describe how how a a crystalline crystalline sample sample of of copper( copper(II II)) ethanoate ethanoate can can be be prepared prepared starting starting with with ethanoic acid acid and and copper( copper(II II)) carbonate. carbonate. ethanoic abul fazal ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... ....................................................................................................................................... [3] [3] (iii) (iii) Write the the word word equation equation for for the the reaction reaction between between ethanoic ethanoic acid acid and and copper( copper(II II)) carbonate. carbonate. Write ....................................................................................................................................... [1] [1] ....................................................................................................................................... [Total: [Total: 18] 18] © © UCLES UCLES 2018 2018 Organic Chemistry WS 2 0620/43/M/J/18 0620/43/M/J/18 Abul Fazal 11 1187 5 Alcohols are a ‘family’ of organic molecules which 11 have the same general formula. 5 Alcohols are a ‘family’ of organic molecules which 11 have the same general formula. 17 (a) What is P42 the name to any ‘family’which of organic molecules which have the same general MAR Q05ofgiven 5 2018 Alcohols are a ‘family’ organic molecules have the same general formula. formula and similar chemical properties? (a) Whatare is the nameofgiven to any ‘family’which of organic molecules which have the same general 5 Alcohols a ‘family’ organic molecules have the same general formula. chemical properties? (a) formula What is and the similar name given to any ‘family’ of organic molecules which have the same general .............................................................................................................................................. [1] formula chemical properties? (a) What is and the similar name given to any ‘family’ of organic molecules which have the same general .............................................................................................................................................. [1] formula and similar chemical properties? .............................................................................................................................................. [1] (b) Give the general formula of alcohols. .............................................................................................................................................. [1] (b) Give the general formula of alcohols. .............................................................................................................................................. [1] (b) Give the general formula of alcohols. .............................................................................................................................................. [1] (b) Give the general formula of alcohols. .............................................................................................................................................. [1] (c) Propan-1-ol can be made from propene. .............................................................................................................................................. [1] (c) Propan-1-ol can be made from propene. Name the reagent andfrom givepropene. the conditions needed to convert propene into propan-1-ol. (c) (i) Propan-1-ol can be made (i) Name the reagent and give the conditions needed to convert propene into propan-1-ol. (c) Propan-1-ol can be made from propene. (i) reagent Name the............................................................................................................................... reagent and give the conditions needed to convert propene into propan-1-ol. (i) reagent Name the............................................................................................................................... reagent and give the conditions needed to convert propene into propan-1-ol. conditions ........................................................................................................................... reagent ............................................................................................................................... [2] conditions ........................................................................................................................... reagent ............................................................................................................................... [2] conditions ........................................................................................................................... (ii) conditions Write a chemical equation for the complete combustion of propan-1-ol. [2] ........................................................................................................................... (ii) Write a chemical equation for the complete combustion of propan-1-ol. [2] ....................................................................................................................................... [2] (ii) Write a chemical equation for the complete combustion of propan-1-ol. ....................................................................................................................................... [2] (ii) Write a chemical equation for the complete combustion of propan-1-ol. ....................................................................................................................................... [2] (d) A simple sugar can be represented as shown. ....................................................................................................................................... [2] (d) A simple sugar can be represented as shown. (d) A simple sugar can be represented H O as shown. O H (d) A simple sugar can be represented H O as shown. O H H O O H carbohydrates. Simple sugars can be polymerised to make more complex H O O H Simple sugars can be polymerised to make more complex carbohydrates. (i) Complete the diagram to showtopart of more a carbohydrate polymer made from the simple Simple sugars can be polymerised make complex carbohydrates. sugar shown. (i) Complete the diagram to show part of a carbohydrate polymer made from the simple Simple sugars can be polymerised to make more complex carbohydrates. shown. (i) sugar Complete the diagram to show part of a carbohydrate polymer made from the simple shown. (i) sugar Complete the diagram to show part of a carbohydrate polymer made from the simple sugar shown. abul fazal (ii) (ii) (ii) (ii) (iii) (iii) (iii) (iii) [2] [2] Name the chemical process which occurs when a carbohydrate polymer is broken down [2] into simple sugars. process which occurs when a carbohydrate polymer is broken down Name the chemical [2] into simple sugars. process which occurs when a carbohydrate polymer is broken down Name the chemical ....................................................................................................................................... [1] into simple sugars. process which occurs when a carbohydrate polymer is broken down Name the chemical ....................................................................................................................................... [1] into simple sugars. What conditions are needed for this process to occur? ....................................................................................................................................... [1] What conditions are needed for this process to occur? ....................................................................................................................................... [1] ....................................................................................................................................... [1] What conditions are needed for this process to occur? ....................................................................................................................................... [1] What conditions are needed for this process to occur? ....................................................................................................................................... [1] ....................................................................................................................................... [1] © UCLES 2018 0620/42/F/M/18 © UCLES 2018 0620/42/F/M/18 © UCLES 2018 0620/42/F/M/18 © UCLES 2018 0620/42/F/M/18 Abul Fazal [Turn over [Turn over [Turn over [Turn over Organic Chemistry WS 2 88 12 12 18 NOV P41 6 2018 (a) Ethane, C2H6,Q06 is a member of the homologous series called alkanes. a member of homologous the homologous series called alcohols. C22HH65,OH, 6 (a) Ethanol, Ethane, C is a is member of the series called alkanes. Ethanol, C2H5OH, is a member of the homologous series called alcohols. (i) Alkanes are hydrocarbons. (i) Alkanes are hydrocarbons. What is meant by the term hydrocarbon? What is meant by the term hydrocarbon? ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... [2] ....................................................................................................................................... [2] (ii) All members of a homologous series can be represented by a general formula. (ii) All members of a homologous series can be represented by a general formula. State the general formula of: State the general formula of: ● alkanes ........................................................................................................................ ● alkanes ........................................................................................................................ ● alcohols ........................................................................................................................ [2] ● alcohols ........................................................................................................................ [2] (iii) State two characteristics, other than having the same general formula, of members of a series. (iii) homologous State two characteristics, other than having the same general formula, of members of a homologous series. 1 .......................................................................................................................................... 1 .......................................................................................................................................... ............................................................................................................................................. ............................................................................................................................................. 2 .......................................................................................................................................... 2 .......................................................................................................................................... ............................................................................................................................................. [2] ............................................................................................................................................. [2] (b) Ethane can react with chlorine in a substitution reaction. (b) Ethane can react with chlorine in a substitution reaction. (i) State one essential reaction condition. (i) State one essential reaction condition. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Draw the structure of the organic product formed by substitution of one of the hydrogen in ethane with Show all of the atoms all of theofbonds. (ii) atoms Draw the structure ofchlorine. the organic product formed by and substitution one of the hydrogen atoms in ethane with chlorine. Show all of the atoms and all of the bonds. abul fazal (iii) (iii) [1] [1] Name the product of the substitution reaction between ethane and chlorine that does not contain carbon. Name the product of the substitution reaction between ethane and chlorine that does not contain carbon. ....................................................................................................................................... [1] ....................................................................................................................................... [1] © UCLES 2018 0620/41/O/N/18 © UCLES 2018 0620/41/O/N/18 Organic Chemistry WS 2 Abul Fazal 13 89 13 (c) Propan-1-ol is an alcohol. (c) Propan-1-ol is an alcohol. The structure of propan-1-ol is shown. The structure of propan-1-ol is shown. H H H H H C C H C C H H H H H H C C H H O O H H Propan-1-ol reacts with ethanoic acid to form an ester. Propan-1-ol reacts with ethanoic acid to form an ester. Give the name of the ester formed in this reaction. Give the name of the ester formed in this reaction. .............................................................................................................................................. [1] .............................................................................................................................................. [1] (d) Ester Y has the structure shown. (d) Ester Y has the structure shown. H H (i) (i) (ii) (ii) H H C C H H H H C C H H H HH H C C O C C O H H H H ester Y ester Y O O C C H H Give the molecular formula of ester Y. Give the molecular formula of ester Y. ....................................................................................................................................... [1] ....................................................................................................................................... [1] Draw the structures of the carboxylic acid and the alcohol used to make ester Y. Show all Draw structures acid theof alcohol used to make ester Show all of the the atoms and all of the carboxylic bonds. Give theand name the carboxylic acid and theY.alcohol. of the atoms and all of the bonds. Give the name of the carboxylic acid and the alcohol. structure of the carboxylic acid structure of the carboxylic acid abul fazal name of the carboxylic acid ................................................................................................ name of the carboxylic acid ................................................................................................ structure of the alcohol structure of the alcohol name of the alcohol ............................................................................................................ name of the alcohol ............................................................................................................ [4] [4] © UCLES 2018 © UCLES 2018 Abul Fazal 0620/41/O/N/18 0620/41/O/N/18 [Turn over [Turn over Organic Chemistry WS 2 11 1190 11 hydrocarbons. 5 Alkynes are a homologous series of unsaturated 11 hydrocarbons. 5 Alkynes are a homologous series of unsaturated All members contain a C≡C triple bond. 19 NOV Q05 5 2018 Alkynes are aP42 homologous of unsaturated hydrocarbons. All members contain a C≡Cseries triple bond. 5 Alkynes are acontain homologous series of unsaturated hydrocarbons. All a C≡C tripleinformation bond. (a) members Complete the table showing about the first three alkynes. All members contain a C≡C triple bond. (a) Complete the table showing information about the first three alkynes. (a) Complete the table showing information about the first three alkynes. (a) Complete first three alkynes. formulathe table showing C2H2 information aboutCthe 3H 4 formula C 2H 2 C 3H 4 formula C 2H 2 C 3H 4 structure H–C≡C–H H–C≡C–CH H–C≡C–CH2–CH3 formula C H C 3H 4 3 2 2 structure H–C≡C–H H–C≡C–CH H–C≡C–CH2–CH3 3 structure H–C≡C–H H–C≡C–CH3 H–C≡C–CH2–CH3 name ethyne butyne –CH structure H–C≡C–H H–C≡C–CH H–C≡C–CH 3 3 name ethyne butyne2 name ethyne butyne name ethyne butyne [2] [2] [2] [2] (b) Complete the dot-and-cross diagram to show the electron arrangement in a molecule of ethyne, (b) Complete the dot-and-cross diagram to show the electron arrangement in a molecule of ethyne, H–C≡C–H. Show outer shell electrons only. (b) Complete dot-and-cross to only. show the electron arrangement in a molecule of ethyne, H–C≡C–H.the Show outer shelldiagram electrons (b) Complete dot-and-cross to only. show the electron arrangement in a molecule of ethyne, H–C≡C–H.the Show outer shelldiagram electrons H–C≡C–H. Show outer shell electrons only. H H H H C C C C C C C C H H H H [2] [2] [2] [2] (c) Compounds in the same homologous series have the same general formula. (c) Compounds in the same homologous series have the same general formula. (c) (i) Compounds the same homologous series have same general formula. Give twoinother characteristics of members of athe homologous series. (c) (i) Compounds in the same homologous series have the same general formula. Give two other characteristics of members of a homologous series. (i) Give two other characteristics of members of a homologous series. 1 .......................................................................................................................................... (i) Give two other characteristics of members of a homologous series. 1 .......................................................................................................................................... 1 .......................................................................................................................................... 2 .......................................................................................................................................... 1 2 .......................................................................................................................................... .......................................................................................................................................... [2] 2 .......................................................................................................................................... [2] 2 .......................................................................................................................................... [2] (ii) Use the information in the table in (a) to deduce the general formula of alkynes. [2] (ii) Use the information in the table in (a) to deduce the general formula of alkynes. (ii) Use the information in the table in (a) to deduce the general formula of alkynes. ....................................................................................................................................... [1] (ii) Use the information in the table in (a) to deduce the general formula of alkynes. ....................................................................................................................................... [1] ....................................................................................................................................... [1] ....................................................................................................................................... [1] (d) Alkynes are unsaturated. (d) Alkynes are unsaturated. (d) Alkynes unsaturated. Describeare a test for unsaturation. (d) Alkynes unsaturated. Describeare a test for unsaturation. Describe a test for unsaturation. test ............................................................................................................................................. Describe a test for unsaturation. test ............................................................................................................................................. test result............................................................................................................................................. .......................................................................................................................................... test result............................................................................................................................................. .......................................................................................................................................... [2] 12 result .......................................................................................................................................... [2] result .......................................................................................................................................... [2] (e) (i) Name an oxidising agent which can be used to oxidise ethanol to ethanoic acid. [2] abul fazal ....................................................................................................................................... [2] (ii) © UCLES 2018 © UCLES 2018 © UCLES 2018 © UCLES 2018 Draw the structure of ethanoic acid. Show all of the atoms and all of the bonds. [Turn over 0620/42/O/N/18 [Turn over 0620/42/O/N/18 [Turn over 0620/42/O/N/18 [Turn over 0620/42/O/N/18 [1] Organic WS 2 can be converted into esters. (f) Chemistry Carboxylic acids (i) Abul Fazal The ester formed by reacting propanoic acid and methanol has the molecular formula [1] [1] 91 (f) Carboxylic acids can be converted into esters. (f) Carboxylic acids can be converted into esters. (i) The ester formed by reacting propanoic acid and methanol has the molecular formula (i) C The ester formed by reacting propanoic acid and methanol has the molecular formula 4H8O2. C4H8O2. Name this ester and draw its structure. Show all of the atoms and all of the bonds. Name this ester and draw its structure. Show all of the atoms and all of the bonds. name of the ester ................................................................................................................ name of the ester ................................................................................................................ structure of the ester structure of the ester [2] [2] (ii) Name another ester with the molecular formula C4H8O2. (ii) Name another ester with the molecular formula C4H8O2. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (g) Polyesters are polymers. (g) Polyesters are polymers. (i) What type of polymerisation is used in the manufacture of polyesters? (i) What type of polymerisation is used in the manufacture of polyesters? ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Name a polyester. (ii) Name a polyester. ....................................................................................................................................... [1] ....................................................................................................................................... [1] [Total: 17] [Total: 17] abul fazal © UCLES 2018 © UCLES 2018 Abul Fazal 0620/42/O/N/18 0620/42/O/N/18 Organic Chemistry WS 2 92 9 20 2018 NOV P43 Q06 6 (a) Ethanol can be manufactured by fermentation and by hydration. (i) Describe these two processes of ethanol manufacture. In each case you should: ● identify the reactants ● give the reaction conditions ● write a chemical equation for the reaction which produces ethanol. fermentation ........................................................................................................................ ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. hydration ............................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. ............................................................................................................................................. [6] (ii) Give two advantages of ethanol manufacture by fermentation compared to by hydration. 1 .......................................................................................................................................... 2 .......................................................................................................................................... [2] (iii) abul fazal State two major uses of ethanol. 1 .......................................................................................................................................... 2 .......................................................................................................................................... [2] © UCLES 2018 Organic Chemistry WS 2 0620/43/O/N/18 [Turn over Abul Fazal 11 93 11 11 5 The structures of five alkenes, A, B, C, D and E, are shown. 5 2019 The structures ofQ05 five alkenes, A, B, C, D and 11 E, are shown. 21 JUN P41 5 The structures A of five alkenes, A, B, C, D and B E, are shown. C 5 The structures of five alkenes, A, B, C, D and E, are shown. A B C H H H CH3 H CH CH A B C CH2CH3 H H H CH3 H 2 3 H C AC H H C B C CH3 H C C C CH2CH3 H C C H H C C CH3 H C C CH2CH3 H C C H H C C H H C C H H C C H H C CH H C CH H H H H H H D E H H H H H H D E CH2CH2CH3 CH2CH2CH2CH3 H H D CH CH CH E CH2CH2CH2CH3 H H 2 2 3 D H C C CH2CH2CH3 H C E C CH2CH2CH2CH3 H C C CH2CH2CH3 H C C CH2CH2CH2CH3 H C C H H C C H H C C H H C CH H H H H (a) What is the general H formula of H alkenes? H H (a) What is the general formula of alkenes? (a) .............................................................................................................................................. What is the general formula of alkenes? [1] (a) .............................................................................................................................................. What is the general formula of alkenes? [1] .............................................................................................................................................. [1] .............................................................................................................................................. [1] (b) What is the molecular formula of alkene D? (b) What is the molecular formula of alkene D? (b) .............................................................................................................................................. What is the molecular formula of alkene D? [1] (b) .............................................................................................................................................. What is the molecular formula of alkene D? [1] .............................................................................................................................................. [1] .............................................................................................................................................. [1] (c) Predict which alkene, A, B, C, D or E, has the highest boiling point. (c) Explain Predict which alkene, A, B, C, D or E, has the highest boiling point. your answer. (c) Explain Predict which alkene, A, B, C, D or E, has the highest boiling point. your answer. (c) alkene Predict............................. which alkene, A, B, C, D or E, has the highest boiling point. Explain your answer. Explain............................. your answer. alkene alkene ............................. explanation ................................................................................................................................ alkene ............................. explanation ................................................................................................................................ explanation ................................................................................................................................ .................................................................................................................................................... explanation ................................................................................................................................ .................................................................................................................................................... [2] .................................................................................................................................................... [2] .................................................................................................................................................... [2] [2] (d) Which alkene, A, B, C, D or E, diffuses most quickly? (d) Explain Which alkene, A, B, C, D or E, diffuses most quickly? your answer. (d) Explain Which alkene, A, B, C, D or E, diffuses most quickly? your answer. (d) alkene Which alkene, A, B, C, D or E, diffuses most quickly? Explain your answer. ............................. Explain your answer. alkene ............................. alkene ............................. explanation ................................................................................................................................ alkene ............................. explanation ................................................................................................................................ explanation ................................................................................................................................ .................................................................................................................................................... explanation ................................................................................................................................ .................................................................................................................................................... [2] .................................................................................................................................................... [2] .................................................................................................................................................... [2] [2] abul fazal © UCLES 2019 © UCLES 2019 © UCLES 2019 0620/41/M/J/19 0620/41/M/J/19 0620/41/M/J/19 © UCLES 2019 0620/41/M/J/19 Abul Fazal [Turn over [Turn over [Turn over [Turn over Organic Chemistry WS 2 1294 12 (e) A student added aqueous bromine to alkene C. (e) A student added aqueous bromine to alkene C. C C CH CH H 2 3 H CH2CH3 C C C C H H H H Describe the colour change seen and draw the structure of the product. Show all of the atoms Describe and all of the the colour bonds.change seen and draw the structure of the product. Show all of the atoms and all of the bonds. colour change from ........................................................ to ..................................................... colour change from ........................................................ to ..................................................... structure structure [2] [2] (f) Two different alcohols can be produced from alkene B by an addition reaction. (f) Two different alcohols can be produced from alkene B by an addition reaction. B B CH H 3 H CH3 C C C C H H H H (i) (i) (ii) (ii) Draw the structures of the two alcohols. Show all of the atoms and all of the bonds. Draw the structures of the two alcohols. Show all of the atoms and all of the bonds. abul fazal [2] [2] State the reagent and conditions needed to produce an alcohol from alkene B. State the reagent and conditions needed to produce an alcohol from alkene B. reagent ............................................................................................................................... reagent ............................................................................................................................... conditions ........................................................................................................................... conditions ........................................................................................................................... ............................................................................................................................................. ............................................................................................................................................. [3] [3] © UCLES 2019 © UCLES 2019 Organic Chemistry WS 2 0620/41/M/J/19 0620/41/M/J/19 Abul Fazal increasing thethe temperature increasing temperature increases increases decreasing thethe pressure decreasing pressure 95 [4] 22 2019 JUN P42 Q04 (c) (c) Methanol is ais member of of thethe homologous Methanol a member homologousseries seriesofofalcohols. alcohols. State two general characteristicsofofa ahomologous homologousseries. series. (i) (i)State two general characteristics 1 .......................................................................................................................................... 1 .......................................................................................................................................... 2 .......................................................................................................................................... 2 .......................................................................................................................................... [2] [2] Draw structures two differentalcohols, alcohols,each eachcontaining containingthree threecarbon carbon atoms. atoms. Show Show (ii)(ii)Draw thethe structures of of two different all of the atoms and all of the bonds. all of the atoms and all of the bonds. Name these two alcohols. Name these two alcohols. name ...................................................... name ...................................................... name ...................................................... name ...................................................... 7 (iii) © UCLES 2019 © UCLES 2019 [4] [4] What term is used to describe compounds with the same molecular formula but different structural formulae? 0620/42/M/J/19 0620/42/M/J/19 ....................................................................................................................................... [1] (d) Alcohols react with carboxylic acids to produce esters. abul fazal (i) The structure of ester X is shown. O H C O H H C C H H H Name ester X. ....................................................................................................................................... [1] (ii) Give the name of the carboxylic acid and the alcohol that react together to produce ester X. carboxylic acid .................................................................................................................... alcohol ................................................................................................................................ [2] (iii) Ester Y is different from ester X but also has the formula C3H6O2. Draw the structure of ester Y. Show all of the atoms and all of the bonds. Abul Fazal Organic Chemistry WS 2 (iii) What term is used to describe compounds with the same molecular formula but different structural formulae? ....................................................................................................................................... [1] 96 (d) Alcohols react with carboxylic acids to produce esters. (i) The structure of ester X is shown. O H C O H H C C H H H Name ester X. ....................................................................................................................................... [1] (ii) Give the name of the carboxylic acid and the alcohol that react together to produce ester X. carboxylic acid .................................................................................................................... alcohol ................................................................................................................................ [2] (iii) Ester Y is different from ester X but also has the formula C3H6O2. Draw the structure of ester Y. Show all of the atoms and all of the bonds. ............................................................................................................................................. [2] abul fazal [Total: 17] © UCLES 2019 Organic Chemistry WS 2 0620/42/M/J/19 [Turn over Abul Fazal 97 12 12 23 2019 JUN P43 Q06 6 (a) Two hydrocarbons have the structures shown. 6 (a) Two hydrocarbons have the structures shown. hydrocarbon A hydrocarbon A H H H H C C H H H H C C H H C C H H H H C C H H C C H H hydrocarbon B hydrocarbon B H H H H H H C H H C C H C H C H H C C C H C C H H H H H H H H H (i) Why are these two compounds hydrocarbons? (i) Why are these two compounds hydrocarbons? ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... [2] ....................................................................................................................................... [2] (ii) Hydrocarbon B reacts in the same way as a typical alkane. (ii) Hydrocarbon B reacts in the same way as a typical alkane. Describe a chemical test to tell the difference between hydrocarbon A and hydrocarbon B. Describe a chemical test to tell the difference between hydrocarbon A and hydrocarbon B. State the name of the reagent you would use and the result you would obtain with State the name of hydrocarbon the reagent B. you would use and the result you would obtain with hydrocarbon A and hydrocarbon A and hydrocarbon B. reagent ............................................................................................................................... reagent ............................................................................................................................... result with hydrocarbon A ................................................................................................... result with hydrocarbon A ................................................................................................... result with hydrocarbon B ................................................................................................... result with hydrocarbon B ................................................................................................... [3] [3] (b) Alkenes react with steam to form alcohols. (b) Alkenes react with to form alcohols. Compound C is an steam alcohol. Compound C is an alcohol. compound C compound C H H H H H H H H H C C C C H C C C C H H H H H H H H abul fazal O O H H Draw the structure of the alkene which could be reacted with steam to make compound C. Draw of and the alkene which could be reacted with steam to make compound C. Show the all ofstructure the atoms all of the bonds. Show all of the atoms and all of the bonds. [1] [1] © UCLES 2019 © UCLES 2019 Abul Fazal 0620/43/M/J/19 0620/43/M/J/19 Organic Chemistry WS 2 (ii) Why is ethanoic acid described as weak ? ............................................................................................................................................. 98 ....................................................................................................................................... [1] 24 2019 MAR P42 Q04 (d) Ethanoic acid reacts with methanol to form an ester. 5 9 (i) State two conditions required for this reaction. (a) Part of the structure of synthetic polymer A is shown. 1 .......................................................................................................................................... CH3 CH3 CH3 CH3 CH3 CH3 2 .......................................................................................................................................... [2] C C C C C C (ii) CH3 ethanoic CH3 CH3 acid reacts with methanol. Show all Draw the structure of the CH ester formed 3 CH 3 CH3when of the atoms and all of the bonds. Name the ester. (i) What type of synthetic polymer is A? structure ....................................................................................................................................... [1] (ii) Deduce the empirical formula of polymer A. ....................................................................................................................................... [1] (iii) Draw the structure of the monomer from which polymer A is made. name ................................................................................................................................... [3] (iii) Name an ester which is a structural isomer of the ester in (d)(ii). ....................................................................................................................................... [1] [2] 25 2019 NOV P41 Q05 [Total: 15] (b) The formula C4H10 represents two different structural isomers. (i) What is meant by the term structural isomers? ............................................................................................................................................. abul fazal ............................................................................................................................................. ....................................................................................................................................... [2] (ii) © UCLES 2019 Draw the structures of two structural isomers with the formula C4H10. Show all of the atoms and all of the bonds. 0620/42/F/M/19 [2] (iii) All structural isomers of C4H10 are flammable. Write a chemical equation for the incomplete combustion of C4H10. ....................................................................................................................................... [2] [Total: 10] © UCLES 2019 Organic Chemistry WS 2 0620/41/O/N/19 [Turn over Abul Fazal 99 26 2019 NOV P41 Q07 7 12 This question is about ethanol. (a) Ethanol that is suitable for use as a fuel can be manufactured from sugars such as glucose, C6H12O6, by a two-step process. Describe how this can be done. In your answer, include: ● ● ● an equation for the reaction in which ethanol is formed the essential conditions for the reaction in which ethanol is formed the name of the process used to obtain ethanol that is pure enough to use as a fuel from the reaction mixture. .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .................................................................................................................................................... .............................................................................................................................................. [5] abul fazal © UCLES 2019 Abul Fazal 0620/41/O/N/19 Organic Chemistry WS 2 100 10 27 2020 JUN P42 Q06 6 (a) Propane reacts with chlorine in a photochemical reaction as shown. C3H8 + Cl 2 → C3H7Cl + HCl (i) What type of reaction is this? ....................................................................................................................................... [1] (ii) What condition is needed for this photochemical reaction to occur? ....................................................................................................................................... [1] (iii) Draw two structural isomers of compounds with the formula C3H7Cl. Show all of the atoms and all of the bonds. 12 [2] (c) There are three functional groups in compound A. (b) Propene reacts with chlorine in an addition reaction as shown. compound A C3H6 + Cl 2 → C3H6Cl 2 COOH CH2OH (i) State why this is an addition reaction. C C ....................................................................................................................................... [1] H H (i) abul fazal Name the homologous series of compounds that contains the following structures. C=C .................................................................................................................................... –OH .................................................................................................................................... –COOH ............................................................................................................................... [3] (ii) What would you observe when compound A is added to: aqueous bromine ................................................................................................................ aqueous sodium carbonate? .............................................................................................. [2] (d) Compound A can be used as a single monomer to produce two different polymers. © UCLES 2020 (i) 0620/42/M/J/20 Draw one repeat unit of the addition polymer formed from compound A. Organic Chemistry WS 2 Abul Fazal aqueous bromine ................................................................................................................ aqueous sodium carbonate? .............................................................................................. [2] 101 (d) Compound A can be used as a single monomer to produce two different polymers. (i) Draw one repeat unit of the addition polymer formed from compound A. [2] (ii) What type of condensation polymer is formed from compound A? ....................................................................................................................................... [1] [Total: 16] © UCLES 2020 0620/42/M/J/20 abul fazal Abul Fazal Organic Chemistry WS 2 102 2 28 2020 JUN P43 Q01 1 (a) 7KHVWUXFWXUHVRI¿YHRUJDQLFFRPSRXQGVABCDDQGEDUHVKRZQ QVZHUWKHTXHVWLRQVWKDWIROORZ $ (DFKOHWWHUPD\EHXVHGRQFHPRUHWKDQRQFHRUQRWDWDOO A H H H H C C C H H H O C H O H B C H H H H C C C H H H H H C H D H H C C H H E H H H C C C H H H O H H H H C C H H O C O H (i) *LYHWKHOHWWHURIWKHFRPSRXQGWKDWLVSURSDQRO >@ (ii) *LYHWKHOHWWHURIWKHFRPSRXQGWKDWKDVWKHHPSLULFDOIRUPXOD&+2 >@ (iii) *LYHWKHOHWWHURIoneFRPSRXQGWKDWUHDFWVZLWKEURPLQHLQDQDGGLWLRQUHDFWLRQ >@ (iv) *LYHWKHOHWWHURIoneFRPSRXQGWKDWUHDFWVZLWKFKORULQHWRIRUPWKHFRPSRXQGVKRZQ abul fazal H H Cl H C C C H H H H >@ (v) *LYHWKHOHWWHUVRItwoFRPSRXQGVWKDWFDQUHDFWZLWKHDFKRWKHUWRIRUPDQHVWHU DQG>@ (vi) *LYHWKHOHWWHURIWKHFRPSRXQGWKDWLVLQWKHVDPHKRPRORJRXVVHULHVDVKH[HQH >@ (vii) *LYHWKHOHWWHURIoneFRPSRXQGWKDWLVDQDFLG >@ © UCLES 2020 Organic Chemistry WS 2 0620/43/M/J/20 Abul Fazal H H H 103 >@ (v) *LYHWKHOHWWHUVRItwoFRPSRXQGVWKDWFDQUHDFWZLWKHDFKRWKHUWRIRUPDQHVWHU DQG>@ (vi) *LYHWKHOHWWHURIWKHFRPSRXQGWKDWLVLQWKHVDPHKRPRORJRXVVHULHVDVKH[HQH >@ (vii) *LYHWKHOHWWHURIoneFRPSRXQGWKDWLVDQDFLG 3 >@ (viii) 'UDZDVWUXFWXUDOLVRPHURIFRPSRXQGD 0620/43/M/J/20 © UCLES 2020 6KRZDOORIWKHDWRPVDQGDOORIWKHERQGV >@ 2 (b) 6RPHDFLGVDUHGHVFULEHGDVZHDNDFLGV Petroleum is a useful natural resource. 6WDWHWKHPHDQLQJRIWKHWHUPweak acid The diagram shows how petroleum can be separated into useful substances. ZHDN refinery gas 29 2020 MAR P42 Q01 1 DFLG >@ gasoline fraction abul fazal A >7RWDO@ kerosene fraction diesel oil fuel oil fraction lubricating oil fraction petroleum B (a) What is the name of the separation process shown in the diagram? .............................................................................................................................................. [2] (b) Name the fraction leaving at: A ................................................................................................................................................ Abul Fazal B ................................................................................................................................................ Organic Chemistry WS 2 [2] (a) What is the name of the separation process shown in the diagram? .............................................................................................................................................. [2] .............................................................................................................................................. [2] 104 (b) Name the fraction leaving at: (b) Name the fraction leaving at: A ................................................................................................................................................ A ................................................................................................................................................ B ................................................................................................................................................ [2] B ................................................................................................................................................ [2] (c) Refinery gas is a mixture of hydrocarbons. (c) Refinery gas is a mixture of hydrocarbons. One refinery gas is butane, C4H10. One refinery gas is butane, C4H10. (i) Suggest the names of two other refinery gases. (i) Suggest the names of two other refinery gases. ............................................................... and .............................................................. [2] ............................................................... and .............................................................. [2] (ii) Write the chemical equation for the complete combustion of butane. (ii) Write the chemical equation for the complete combustion of butane. ....................................................................................................................................... [2] ....................................................................................................................................... [2] (iii) Name the toxic gas produced by the incomplete combustion of butane. (iii) Name the toxic gas produced by the incomplete combustion of butane. 3 ....................................................................................................................................... [1] 3 ....................................................................................................................................... [1] (d) Gasoline and kerosene are both fuels. They have different properties. (d) Gasoline and kerosene are both fuels. They have different properties. (i) Describe the differences in the properties given. (i) Describe the differences in the properties given. © UCLES 2020 © UCLES 2020 viscosity of the fuel ............................................................................................................. 0620/42/F/M/20 viscosity of the fuel ............................................................................................................. 0620/42/F/M/20 ............................................................................................................................................. ............................................................................................................................................. flammability of the fuel ........................................................................................................ flammability of the fuel ........................................................................................................ ............................................................................................................................................. ............................................................................................................................................. [2] [2] (ii) What difference in the molecules of gasoline and kerosene causes these differences in (ii) properties? What difference in the molecules of gasoline and kerosene causes these differences in properties? abul fazal ....................................................................................................................................... [1] ....................................................................................................................................... [1] (e) Hydrogen fuel cells can be used to power vehicles. (e) Hydrogen fuel cells can be used to power vehicles. Write the word equation for the overall reaction that takes place in a hydrogen fuel cell. Write the word equation for the overall reaction that takes place in a hydrogen fuel cell. .............................................................................................................................................. [1] .............................................................................................................................................. [1] [Total: 13] [Total: 13] Organic Chemistry WS 2 Abul Fazal 12 105 12 12of the same homologous series. 6 (a) Ethane, propane and butane are members 30 NOV P41 Q06 6 2020 (a) Ethane, propane and butane are members of the same homologous series. 6 (a) (i) Ethane, propane and butaneseries. are members of the same homologous series. Name this homologous (i) Name this homologous series. (i) Name this homologous series. ....................................................................................................................................... [1] ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) State two ways members of the same homologous series are similar. (ii) State two ways members of the same homologous series are similar. (ii) 1 State two ways members of the same homologous series are similar. .......................................................................................................................................... 1 .......................................................................................................................................... 1 2 .......................................................................................................................................... 2 .......................................................................................................................................... [2] [2] 2 .......................................................................................................................................... [2] (b) One mole of ethane, C2H6, contains 6.02 × 1023 molecules. (b) One mole of ethane, C2H6, contains 6.02 × 1023 molecules. 23 6.02 10ethane. molecules. (b) Calculate One mole how of ethane, C2H6, contains many molecules are in 15 g× of Calculate how many molecules are in 15 g of ethane. Calculate how many molecules are in 15 g of ethane. number of ethane molecules = .............................. [1] number of ethane molecules = .............................. [1] number of ethane molecules = .............................. [1] (c) Propane reacts with chlorine. (c) Propane reacts with chlorine. (c) (i) Propane with chlorine. Writereacts the formula of the product which does not contain carbon. (i) Write the formula of the product which does not contain carbon. (i) Write the formula of the product which does not contain carbon. ....................................................................................................................................... [1] ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Draw the structure of an organic product formed. Show all of the atoms and all of the (ii) Draw the structure of an organic product formed. Show all of the atoms and all of the bonds. (ii) bonds. Draw the structure of an organic product formed. Show all of the atoms and all of the bonds. abul fazal (iii) (iii) (iii) State the name of this type of reaction. State the name of this type of reaction. State the name of this type of reaction. ....................................................................................................................................... [1] ....................................................................................................................................... [1] ....................................................................................................................................... [1] © UCLES 2020 © UCLES 2020 0620/41/O/N/20 0620/41/O/N/20 © UCLES 2020 0620/41/O/N/20 Abul Fazal [1] [1] [1] Organic Chemistry WS 2 13 106 13 (d) (i) Aqueous bromine was added to a sample of ethene. (d) (i) Aqueous bromine was added to a sample of ethene. Give the colour change seen. Give the colour change seen. from ............................................................. to ............................................................ [2] from ............................................................. to ............................................................ [2] (ii) Explain, in terms of bonding, why there is no colour change when aqueous bromine is (ii) added Explain, terms of bonding, why there is no colour change when aqueous bromine is to in ethane. added to ethane. ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (e) There are two structural isomers with the formula C4H10. (e) There are two structural isomers with the formula C4H10. (i) Draw the structures of both of these isomers, showing all of the atoms and all of the bonds. (i) Draw the structures of both of these isomers, showing all of the atoms and all of the bonds. [2] [2] (ii) Butane is formed when longer chain hydrocarbons are cracked. (ii) Butane is formed when longer chain hydrocarbons are cracked. Complete the chemical equation to show the other product when butane is formed by Complete the chemical equation to show the other product when butane is formed by cracking. cracking. [1] C6H14 → C4H10 + ................................ [1] C6H14 → C4H10 + ................................ abul fazal © UCLES 2020 0620/41/O/N/20 © UCLES 2020 0620/41/O/N/20 Organic Chemistry WS 2 [Turn over [Turn over Abul Fazal 107 14 (f) A compound contains 85.7% carbon and 14.3% hydrogen by mass. (i) Calculate the empirical formula of this compound. Show your working. .............................. [2] (ii) The molecular mass of the compound is 112. Calculate the molecular formula of this compound. .............................. [1] 15 15 [Total: 16] 31 2020 NOV P41 Q07 7 (a) Ethanol can be manufactured by two different methods. 7 (a) Ethanol can be manufactured by two different methods. Method 1: fermentation of a sugar, C6H12O6 Method 1: fermentation of a sugar, C6H12O6 C6H12O6 → 2C2H5OH + 2CO2 C6H12O6 → 2C2H5OH + 2CO2 Method 2: reaction of ethene with steam Method 2: reaction of ethene with steam C2H4 + H2O → C2H5OH C2H4 + H2O → C2H5OH (i) Give one advantage of using fermentation compared with Method 2. (i) Give one advantage of using fermentation compared with Method 2. ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Give one disadvantage of using fermentation compared with Method 2. (ii) Give one disadvantage of using fermentation compared with Method 2. ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... [1] ....................................................................................................................................... [1] abul fazal (b) Ethanol reacts with acidified potassium manganate(VII) to form water and a product that turns (b) litmus Ethanol reacts with acidified potassium manganate(VII) to form water and a product that turns red. litmus red. (i) State the name of the product that turns the litmus red. (i) State the name of the product that turns the litmus red. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) State the type of reaction that ethanol undergoes when it reacts with acidified (ii) potassium State the manganate( type of reaction VII). that ethanol undergoes when it reacts with acidified potassium manganate(VII). ....................................................................................................................................... [1] [1] © UCLES 2020 ....................................................................................................................................... 0620/41/O/N/20 (c) Ethanol reacts with methanoic acid to form an ester. (c) Ethanol reacts with methanoic acid to form an ester. (i) Name the ester formed in this reaction. (i) Name the ester formed in this reaction. Abul Fazal Organic Chemistry WS 2 ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Draw the structure of the ester formed. (ii) State the type of reaction that ethanol undergoes when it reacts with acidified potassium manganate(VII). ....................................................................................................................................... [1] 108 (c) Ethanol reacts with methanoic acid to form an ester. (i) Name the ester formed in this reaction. ....................................................................................................................................... [1] (ii) Draw the structure of the ester formed. Show all of the atoms and all of the bonds. [1] 16 (d) The table shows the melting points of ethanol and sodium chloride. substance © UCLES 2020 melting point / °C ethanol 0620/41/O/N/20 sodium chloride –114 [Turn over 801 The difference in melting points is due to differences in attractive forces between particles in these substances. Name the type of attractive force in each substance, which is responsible for the difference in melting points. ethanol ....................................................................................................................................... sodium chloride ......................................................................................................................... [2] [Total: 8] abul fazal Organic Chemistry WS 2 Abul Fazal 109 7 7 4 2020 Alkenes and P42 alkanes are homologous series of 7compounds containing carbon and hydrogen atoms. 32 NOV Q04 4 Alkenes and alkanes are homologous series of compounds containing carbon and hydrogen atoms. 4 Alkenes and are homologous series ofmade compounds containing carbon and hydrogen (a) State thealkanes name of the type of compound from carbon and hydrogen atoms only. atoms. (a) State the name of the type of compound made from carbon and hydrogen atoms only. (a) State the name of the type of compound made from carbon and hydrogen atoms only. .............................................................................................................................................. [1] .............................................................................................................................................. [1] .............................................................................................................................................. [1] (b) Alkenes take part in addition reactions. (b) Alkenes take part in addition reactions. (b) (i) Alkenes take part reactions. Describe whatinisaddition meant by the term addition reaction. (i) Describe what is meant by the term addition reaction. (i) Describe what is meant by the term addition reaction. ....................................................................................................................................... [1] ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Draw the structure of the product made in the addition reaction between propene and (ii) Draw the Show structure theatoms product in the addition reaction between propene and bromine. all ofofthe andmade all of the bonds. bromine. all ofofthe andmade all of the bonds. (ii) Draw the Show structure theatoms product in the addition reaction between propene and bromine. Show all of the atoms and all of the bonds. (iii) (iii) (iii) (iv) (iv) (iv) (c) (c) (c) [2] [2] [2] Describe the colour change seen when propene is added to aqueous bromine. Describe the colour change seen when propene is added to aqueous bromine. Describe the colour change seen when propene is added to aqueous bromine. from ............................................................ to ............................................................ [2] from ............................................................ to ............................................................ [2] from ............................................................ to ............................................................ [2] Draw the structures of molecules of two different alkenes which both undergo an addition Draw thewith structures of form molecules of twoShow different which both undergo an addition reaction steam to butan-2-ol. all ofalkenes the atoms and all of the bonds. reaction steam to butan-2-ol. all ofalkenes the atoms and all of the bonds. Draw thewith structures of form molecules of twoShow different which both undergo an addition reaction with steam to form butan-2-ol. Show all of the atoms and all of the bonds. abul fazal Propane undergoes a substitution reaction with chlorine. Propane undergoes a substitution reaction with chlorine. Propane substitution reaction with between chlorine. one molecule of propane and one Write theundergoes chemical a equation for the reaction Write the chemical equation for the reaction between one molecule of propane and one molecule of chlorine. molecule chlorine.equation for the reaction between one molecule of propane and one Write the ofchemical molecule of chlorine. .............................................................................................................................................. [2] .............................................................................................................................................. [2] .............................................................................................................................................. [2] [Total: 10] [Total: 10] [Total: 10] © UCLES 2020 © UCLES 2020 0620/42/O/N/20 0620/42/O/N/20 © UCLES 2020 0620/42/O/N/20 Abul Fazal [2] [2] [2] [Turn over [Turn over [Turn over Organic Chemistry WS 2 110 8 33 2020 NOV P42 Q05 5 This question is about alcohols, carboxylic acids and esters. (a) Ethanol will react with hot aqueous potassium manganate(VII) to form ethanoic acid. (i) State the other condition needed for this reaction to take place. ....................................................................................................................................... [1] (ii) State the type of chemical change that happens to the ethanol during this reaction. ....................................................................................................................................... [1] (iii) The structure of ethanoic acid is shown. H H C H O C O H Complete the dot-and-cross diagram to show the electron arrangement in a molecule of ethanoic acid. O H H C C H O H abul fazal © UCLES 2020 Organic Chemistry WS 2 [3] 0620/42/O/N/20 Abul Fazal magnesium ribbon is added [6] 111 (c) Ethanoic acid will react with an alcohol to form the ester shown. H H H O H C H C C O C H H C H H H (i) Name the other product formed when ethanoic acid reacts with an alcohol to make this ester. ....................................................................................................................................... [1] (ii) Give one condition needed when ethanoic acid reacts with the alcohol to make this ester. ....................................................................................................................................... [1] (iii) Draw the structure of the alcohol which was added to ethanoic acid to make this ester. Show all of the atoms and all of the bonds. [2] © UCLES 2020 [Turn over 0620/42/O/N/20 abul fazal Abul Fazal Organic Chemistry WS 2 112 12 34 2020 NOV P43 Q06 6 (a) A carboxylic acid and an ester are structural isomers. (i) State the meaning of the term structural isomers. ............................................................................................................................................. ............................................................................................................................................. ....................................................................................................................................... [2] (ii) Draw the structures of the carboxylic acid and the ester which both contain two carbon atoms. Show all of the atoms and all of the bonds. Name the carboxylic acid and the ester. carboxylic acid ester name ................................................ name ................................................ abul fazal © UCLES 2020 Organic Chemistry WS 2 [4] 0620/43/O/N/20 Abul Fazal 113 13 13 35 2021 JUN P41 Q07 7 Many organic compounds contain carbon, hydrogen and oxygen only. 7 Many organic compounds contain carbon, hydrogen and oxygen only. (a) An organic compound V has the following composition by mass. (a) An organic compound V has the following composition by mass. C, 48.65%; H, 8.11%; O, 43.24% C, 48.65%; H, 8.11%; O, 43.24% Calculate the empirical formula of compound V. Calculate the empirical formula of compound V. empirical formula = .............................. [3] empirical formula = .............................. [3] (b) Compound W has the empirical formula CH4O and a relative molecular mass of 32. (b) Compound W has the empirical formula CH4O and a relative molecular mass of 32. Calculate the molecular formula of compound W. Calculate the molecular formula of compound W. molecular formula = .............................. [1] molecular formula = .............................. [1] (c) Compounds X and Y have the same general formula. (c) Compounds X and Y have the same general formula. X and Y are both carboxylic acids. X and Y are both carboxylic acids. Compound X has the molecular formula C2H4O2. Compound X has the molecular formula C2H4O2. Compound Y has the molecular formula C4H8O2. Compound Y has the molecular formula C4H8O2. (i) Deduce the general formula of compounds X and Y. (i) Deduce the general formula of compounds X and Y. ....................................................................................................................................... [1] ....................................................................................................................................... [1] abul fazal © UCLES 2021 © UCLES 2021 Abul Fazal 0620/41/M/J/21 0620/41/M/J/21 [Turn over [Turn over Organic Chemistry WS 2 molecular formula = .............................. [1] 114 (c) Compounds X and Y have the same general formula. X and Y are both carboxylic acids. Compound X has the molecular formula C2H4O2. Compound Y has the molecular formula C4H8O2. (i) Deduce the general formula of compounds X and Y. 14 ....................................................................................................................................... [1] (ii) Draw the structure of compound Y. Show all of the atoms and all of the bonds. Name compound Y. © UCLES 2021 (iii) name ................................................................................................................................... [3] [Turn over 0620/41/M/J/21 Give the name used to describe a ‘family’ of similar compounds with the same general formula, similar chemical properties and the same functional group. ....................................................................................................................................... [1] (d) Propene is an unsaturated hydrocarbon. The formula of propene is shown. CH3CH=CH2 (i) State the colour change observed when propene is added to aqueous bromine. abul fazal from ............................................................. to ............................................................ [1] (ii) Propene can be produced by cracking long chain alkanes. Pentadecane, C15H32, is cracked to produce an alkane and propene in a 1 : 2 molar ratio. Complete the chemical equation for this reaction. C15H32 → ....................................... + ....................................... (iii) [2] Propene can be converted into poly(propene). Name the type of polymerisation that occurs when propene is converted into poly(propene). ....................................................................................................................................... [1] (iv) Complete the diagram to show a section of poly(propene). C Organic Chemistry WS 2 C C C [2]Fazal Abul [Total: 15] formula, similar chemical properties and the same functional group. ....................................................................................................................................... [1] 115 (d) Propene is an unsaturated hydrocarbon. The formula of propene is shown. CH3CH=CH2 (i) State the colour change observed when propene is added to aqueous bromine. from ............................................................. to ............................................................ [1] (ii) Propene can be produced by cracking long chain alkanes. Pentadecane, C15H32, is cracked to produce an alkane and propene in a 1 : 2 molar ratio. Complete the chemical equation for this reaction. C15H32 → ....................................... + ....................................... (iii) [2] Propene can be converted into poly(propene). Name the type of polymerisation that occurs when propene is converted into poly(propene). ....................................................................................................................................... [1] (iv) Complete the diagram to show a section of poly(propene). C C C C [2] [Total: 15] abul fazal © UCLES 2021 Abul Fazal 0620/41/M/J/21 Organic Chemistry WS 2 116 12 12 36 JUN P43 Q07 contain carbon, hydrogen and oxygen only. 7 2021 Many organic compounds 7 Many organic compounds contain carbon, hydrogen and oxygen only. (a) An organic compound R has the following composition by mass. (a) An organic compound R has the following composition by mass. C, 69.77%; H, 11.63%; O, 18.60% C, 69.77%; H, 11.63%; O, 18.60% Calculate the empirical formula of compound R. Calculate the empirical formula of compound R. empirical formula = .............................. [2] empirical formula = .............................. [2] (b) Compound S has the empirical formula CH2O and a relative molecular mass of 60. (b) Compound S has the empirical formula CH2O and a relative molecular mass of 60. Calculate the molecular formula of compound S. Calculate the molecular formula of compound S. molecular formula = .............................. [2] molecular formula = .............................. [2] (c) Compounds T and V have the same molecular formula, C3H6O2. (c) Compounds T and V have the same molecular formula, C3H6O2. ● Compound T is an ester. ● Compound T an ester. V is contains a –COOH functional group. ● Compound V contains a –COOH functional group. (i) State the name given to compounds with the same molecular formula but different (i) structures. State the name given to compounds with the same molecular formula but different structures. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Name the homologous series that V is a member of. (ii) Name the homologous series that V is a member of. ....................................................................................................................................... [1] ....................................................................................................................................... [1] abul fazal © UCLES 2021 © UCLES 2021 Organic Chemistry WS 2 0620/43/M/J/21 0620/43/M/J/21 Abul Fazal 117 molecular formula = .............................. [2] (c) Compounds T and V have the same molecular formula, C3H6O2. ● ● Compound T is an ester. Compound V contains a –COOH functional group. (i) State the name given to compounds with the same molecular formula but different structures. ....................................................................................................................................... [1] (ii) (iii) (iii) © UCLES (iv) 2021 (iv) Name the homologous series that V is a member of. 13 13 ....................................................................................................................................... [1] Draw a structure of compound T. Show all of the atoms and all of the bonds. Draw a structure of compound T. Show all of the atoms and all of the bonds. Name compound T. Name compound T. name ................................................................................................................................... name ................................................................................................................................... [3] [3] 0620/43/M/J/21 Draw the structure of compound V. Show all of the atoms and all of the bonds. Draw the structure of compound V. Show all of the atoms and all of the bonds. Name compound V. Name compound V. name ................................................................................................................................... name ................................................................................................................................... [2] [2] abul fazal (d) Ethanol can be produced from long chain alkanes such as decane, C10H22, in a two-step (d) Ethanol process. can be produced from long chain alkanes such as decane, C10H22, in a two-step process. step 1 step 2 decane step 1 ethene step 2 ethanol ethene ethanol decane For each of the two steps: For thetype twoof steps: ● each nameofthe chemical reaction that occurs ● name the type of chemical reaction that occurs ● write a chemical equation. ● write a chemical equation. step 1: decane to ethene step 1: decane to ethene type of reaction .......................................................................................................................... type of reaction .......................................................................................................................... chemical equation ...................................................................................................................... chemical equation ...................................................................................................................... step 2: ethene to ethanol step 2: ethene to ethanol type of reaction .......................................................................................................................... type of reaction .......................................................................................................................... chemical equation ...................................................................................................................... chemical equation ...................................................................................................................... [4] [4] [Total: 15] [Total: 15]WS 2 Abul Fazal Organic Chemistry 118 8 37 2021 MAR P42 Q05 5 5 The The table table shows shows the the names names or or structures structures of of organic organic compounds compounds P P to to U. U. H H H P P H H H C C C C C C H H H H H Q Q R R propanoic acid but-1-ene T U H H H H S H propan-1-ol propan-1-ol C methyl methyl butanoate butanoate C H H C H H (a) Give the letters of the organic compounds, P to U, that are unsaturated hydrocarbons. .............................................................................................................................................. [2] (b) Describe the test for an unsaturated hydrocarbon. test ............................................................................................................................................. observations .............................................................................................................................. [2] (c) But-1-ene is an unbranched molecule. (i) Name the unbranched isomer of but-1-ene. ....................................................................................................................................... [1] (ii) Draw Draw the structure of a branched isomer of but-1-ene. Show all of the atoms and all of the bonds. bonds. abul fazal [1] [1] (d) (d) Dodecane Dodecane is is an an alkane alkane with with 12 12 carbon carbon atoms. atoms. Dodecane Dodecane can can be be cracked. cracked. (i) (i) Write Write the the formula formula of of dodecane. dodecane. ....................................................................................................................................... ....................................................................................................................................... [1] [1] (ii) (ii) Give Give the the letters letters of of all all the the organic organic compounds, compounds, P P to to U, U, that that can can be be formed formed when when dodecane dodecane is cracked. is cracked. ....................................................................................................................................... ....................................................................................................................................... [2] [2] © © UCLES UCLES 2021 2021 Organic Chemistry WS 2 0620/42/F/M/21 0620/42/F/M/21 Abul Fazal 9 9 9119 needed to convert organic compound U into (e) Name the reagent and suggest the conditions (e) organic Name the reagent S. and suggest the conditions needed to convert organic compound U into compound (e) organic Name the reagent S. and suggest the conditions needed to convert organic compound U into compound organic compound S. reagent ...................................................................................................................................... reagent ...................................................................................................................................... reagent ...................................................................................................................................... conditions .................................................................................................................................. conditions .................................................................................................................................. [3] conditions .................................................................................................................................. [3] [3] (f) (f) (f) Organic compound S can be converted to organic compound Q by reaction with an acidified Organic compound S can be converted to organic compound Q by reaction with an acidified reagent. Organic compound S can be converted to organic compound Q by reaction with an acidified reagent. reagent. (i) Name the type of chemical change that happens to organic compound S. (i) Name the type of chemical change that happens to organic compound S. (i) ....................................................................................................................................... Name the type of chemical change that happens to organic compound S. [1] ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Name the acidified reagent added to organic compound S. (ii) Name the acidified reagent added to organic compound S. (ii) ....................................................................................................................................... Name the acidified reagent added to organic compound S. [1] ....................................................................................................................................... [1] ....................................................................................................................................... [1] (g) Organic compound T is made by reacting two compounds together. (g) Organic compound T is made by reacting two compounds together. (g) (i) Organic compound T is made by reacting two compounds Name the homologous series that organic compound Ttogether. belongs to. (i) Name the homologous series that organic compound T belongs to. (i) ....................................................................................................................................... Name the homologous series that organic compound T belongs to. [1] ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Name the two compounds which react together to make organic compound T. (ii) Name the two compounds which react together to make organic compound T. (ii) Draw Namethe thestructures two compounds react you together make organic T. and all of of eachwhich compound haveto named. Show allcompound of the atoms Draw the structures of each compound you have named. Show all of the atoms and all of the bonds. Draw the structures of each compound you have named. Show all of the atoms and all of the bonds. the bonds. name ................................................................................................................................... name ................................................................................................................................... name ................................................................................................................................... structure structure structure abul fazal name ................................................................................................................................... name ................................................................................................................................... name ................................................................................................................................... structure structure structure [4] [4] [4] (iii) Deduce the molecular formula of organic compound T. (iii) Deduce the molecular formula of organic compound T. (iii) ....................................................................................................................................... Deduce the molecular formula of organic compound T. [1] ....................................................................................................................................... [1] ....................................................................................................................................... [1] [Total: 20] [Total: 20] [Total: 20] [Turn over © UCLES 2021 0620/42/F/M/21 [Turn over © UCLES 2021 0620/42/F/M/21 [Turn over © UCLES 2021 0620/42/F/M/21 Abul Fazal Organic Chemistry WS 2 120 10 38 2021 NOV P41 Q05 5 Alkenes and carboxylic acids are both families of similar compounds with similar chemical properties. Alkenes and carboxylic acids have different reactions. (a) State the term used for a ‘family’ of similar compounds. .............................................................................................................................................. [1] (b) State the general formula of alkenes. .............................................................................................................................................. [1] (c) The structure of but-2-ene is shown. H H H C C H (i) H C C H H H But-2-ene reacts with aqueous bromine in an addition reaction. Describe the colour change seen when but-2-ene is added to aqueous bromine. from ............................................................. to ............................................................ [1] (ii) State what is meant by the term addition reaction. ....................................................................................................................................... [1] (iii) Write the chemical equation for the reaction between but-2-ene and bromine. ....................................................................................................................................... [2] (iv) But-2-ene forms a polymer. Suggest the name of the polymer formed from but-2-ene. abul fazal ....................................................................................................................................... [1] (v) Name and draw a structural isomer of but-2-ene. Show all of the atoms and all of the bonds. name ................................................................................................................................... structure [2] © UCLES 2021 Organic Chemistry WS 2 0620/41/O/N/21 Abul Fazal 121 11 (d) Butanoic acid, CH3CH2CH2COOH, is a carboxylic acid. (i) Deduce the empirical formula of butanoic acid. ....................................................................................................................................... [1] (ii) Complete the chemical equation for the reaction of butanoic acid and sodium carbonate, Na2CO3. 2CH3CH2CH2COOH + Na2CO3 → .................................... + ............... + ............... [2] (iii) Butanoic acid reacts with methanol to form an organic compound and water. ● Name the organic compound formed. ....................................................................................................................................... [1] ● Draw the structure of the organic compound formed. Show all of the atoms and all of the bonds. 11 11 [2] 6 Ethanol, C2H5OH, belongs to the homologous11 series called alcohols. 6 Ethanol, C2H5OH, belongs to the homologous11 series called alcohols. [Total: 15] 39 NOV P42 Q06 6 2021 Ethanol, Cthe H OH, belongs to the homologous series called alcohols. (a) Write general formula of alcohols. 2 5 6 Ethanol, belongs to the homologous series called alcohols. (a) WriteCthe general formula of alcohols. 2H5OH, (a) Write the general formula of alcohols. .............................................................................................................................................. [1] (a) Write the general formula of alcohols. .............................................................................................................................................. [1] .............................................................................................................................................. [1] .............................................................................................................................................. [1] (b) Explain why ethanol cannot be described as a hydrocarbon. (b) Explain why ethanol cannot be described as a hydrocarbon. (b) Explain why ethanol cannot be described as a hydrocarbon. .............................................................................................................................................. [1] (b) Explain why ethanol cannot be described as a hydrocarbon. .............................................................................................................................................. [1] .............................................................................................................................................. [1] .............................................................................................................................................. (c) Ethanol can be manufactured from different substances by reaction with steam or [1] by (c) fermentation. Ethanol can be manufactured from different substances by reaction with steam or by (c) fermentation. Ethanol can be manufactured from different substances by reaction with steam or by (c) (i) Ethanol be manufactured from which different substances bytoreaction with steam or by fermentation. Givecan the formula of the substance reacts with steam form ethanol. fermentation. (i) Give the formula of the substance which reacts with steam to form ethanol. (i) Give the formula of the substance which reacts with steam to form ethanol. ....................................................................................................................................... [1] (i) Give the formula of the substance which reacts with steam to form ethanol. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Name a substance which will undergo fermentation to form ethanol. ....................................................................................................................................... [1] (ii) Name a substance which will undergo fermentation to form ethanol. Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort been made by the publisher which (UCLES) will to trace copyright holders, but if any items clearance have unwittingly been included,[1] the (ii) hasName a substance undergo fermentation torequiring form ethanol. ....................................................................................................................................... publisher will be pleased to make amends at the earliest possible opportunity. (ii) Name a substance which will undergo fermentation to form ethanol. ....................................................................................................................................... [1] To avoid the issue ....................................................................................................................................... of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge [1] Assessment International Education Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download ....................................................................................................................................... [1] (d) Ethanol is a fuel. at www.cambridgeinternational.org after the live examination series. (d) Ethanol is a fuel. Cambridge Assessment International Education is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of the University of (d) Local Ethanol aSyndicate fuel. (UCLES), Write theischemical equation complete combustion of ethanol. Cambridge Examinations whichfor itselfthe is a department of the University of Cambridge. (d) Write Ethanol a fuel. equation for the complete combustion of ethanol. theischemical Write the chemical equation for the complete combustion of ethanol. .............................................................................................................................................. [2] © UCLES 2021 0620/41/O/N/21 Write the chemical equation for the complete combustion of ethanol. .............................................................................................................................................. [2] .............................................................................................................................................. [2] .............................................................................................................................................. [2] abul fazal Abul Fazal Organic Chemistry WS 2 12 122 12 (e) Ethane-1,2-diol has two alcohol functional groups. (e) Ethane-1,2-diol has two alcohol functional groups. H H H H H O C C O H H O C C O H H H H H One molecule of ethane-1,2-diol will react with two molecules of ethanoic acid to form molecule X. One molecule of ethane-1,2-diol will react with two molecules of ethanoic acid to form molecule X. X has two ester functional groups and a molecular formula of C6H10O4. X has two ester functional groups and a molecular formula of C6H10O4. (i) State the empirical formula of X. (i) State the empirical formula of X. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Draw the structure of X. (ii) Draw the structure of X. Show all of the atoms and all of the bonds. Show all of the atoms and all of the bonds. [2] [2] (iii) (iii) Name the other substance formed in this reaction. Name the other substance formed in this reaction. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (f) Each alcohol functional group in ethane-1,2-diol reacts with acidified potassium manganate(VII) form a different organic compound, Y. (f) to Each alcohol functional group in ethane-1,2-diol reacts with acidified potassium manganate(VII) to form a different organic compound, Y. (i) Name the functional groups formed in Y. (i) Name the functional groups formed in Y. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (ii) Draw the structure of Y. (ii) Draw the structure of Y. Show all of the atoms and all of the bonds. Show all of the atoms and all of the bonds. abul fazal [1] [1] [Total: 12] [Total: 12] © UCLES 2021 0620/42/O/N/21 © UCLES 2021 0620/42/O/N/21 Organic Chemistry WS 2 Abul Fazal 12 123 12 7 (a) Ethanol is a member of the homologous series of alcohols. 12 40 NOV P43 Q07 of the homologous series of alcohols. 7 2021 (a) Ethanol is a member Give twoischaracteristics of members of aseries homologous series. 7 (a) Ethanol a member of the homologous of alcohols. Give two characteristics of members of a homologous series. 1 ................................................................................................................................................. Give two characteristics of members of a homologous series. 1 ................................................................................................................................................. 2 ................................................................................................................................................. 1 [2] 2 ................................................................................................................................................. 2 ................................................................................................................................................. [2] [2] (b) Ethanol can be manufactured from ethene. (b) Ethanol can be manufactured from ethene. from longfrom chain hydrocarbons such as decane, C10H22. (b) Ethene Ethanol can can be be made manufactured ethene. Ethene can be made from long chain hydrocarbons such as decane, C10H22. Ethene is then can be converted made frominto longethanol. chain hydrocarbons such as decane, C10H22. Ethene is then converted into ethanol. (i) Name the process used obtain ethene from long chain hydrocarbons such as decane, Ethene is then converted intotoethanol. H . C (i) Name 10 22 the process used to obtain ethene from long chain hydrocarbons such as decane, (i) Name C10H22.the process used to obtain ethene from long chain hydrocarbons such as decane, ....................................................................................................................................... [1] C 10H22. ....................................................................................................................................... [1] (ii) Complete the chemical equation to show the formation of ethene from decane, C10H22. [1] ....................................................................................................................................... (ii) Complete the chemical equation to show the formation of ethene from decane, C10H22. C4H8 + to................... + ................... C10H22 →equation (ii) Complete the chemical show the formation of ethene from decane, C10H22. [2] [2] C10H22 → C4H8 + ................... + ................... (iii) Write the chemical equation the conversion of ethene into ethanol. → C4Hfor + ................... + ................... [2] C10H22 8 (iii) Write the chemical equation for the conversion of ethene into ethanol. ....................................................................................................................................... [1] (iii) Write the chemical equation for the conversion of ethene into ethanol. ....................................................................................................................................... [1] (iv) Name the type of reaction occurring when ethene is converted into ethanol. ....................................................................................................................................... [1] (iv) Name the type of reaction occurring when ethene is converted into ethanol. ....................................................................................................................................... [1] (iv) Name the type of reaction occurring when ethene is converted into ethanol. ....................................................................................................................................... [1] (v) Give one condition for the reaction in which ethene is converted into ethanol. ....................................................................................................................................... [1] (v) Give one condition for the reaction in which ethene is converted into ethanol. ....................................................................................................................................... [1] (v) Give one condition for the reaction in which ethene is converted into ethanol. ....................................................................................................................................... [1] ....................................................................................................................................... [1] (c) Ethanol can also be produced by fermentation of carbohydrates such as glucose. (c) Ethanol can also be produced by fermentation of carbohydrates such as glucose. Give twocan advantages of manufacturing ethanol fermentationsuch compared to manufacturing (c) Ethanol also be produced by fermentation of by carbohydrates as glucose. ethanol from ethene. of manufacturing ethanol by fermentation compared to manufacturing Give two advantages Give two advantages ethanol from ethene. of manufacturing ethanol by fermentation compared to manufacturing 1 ................................................................................................................................................. ethanol from ethene. 1 ................................................................................................................................................. 2 ................................................................................................................................................. 1 [2] 2 ................................................................................................................................................. 2 ................................................................................................................................................. [2] [2] abul fazal © UCLES 2021 0620/43/O/N/21 © UCLES 2021 0620/43/O/N/21 © UCLES 2021 0620/43/O/N/21 Abul Fazal Organic Chemistry WS 2 124 abul fazal Organic Chemistry WS 2 Abul Fazal 32 Abul Fazal Cambridge O Level Chemistry 5070. Syllabus for examination in 2022. 56 Ba barium 137 88 Ra radium – 55 Cs caesium 133 87 Fr francium – Zr Hf lanthanoids Th thorium 232 – 140 90 139 89 Ac cerium lanthanum actinium Ce 58 – La 57 Rf actinoids rutherfordium 104 89–103 178 hafnium 72 91 zirconium 57–71 89 yttrium 48 40 titanium Ti 22 Mn 231 protactinium Pa 91 141 Tc 55 43 Nd 60 – seaborgium Sg 106 184 tungsten W 74 96 238 uranium U 144 92 – neptunium Np – 93 promethium Pm 61 – bohrium Bh 107 186 rhenium Re 75 – molybdenum technetium Mo 52 42 manganese Cr chromium 25 24 praseodymium neodymium Pr 59 – dubnium Db 105 181 tantalum Ta 73 93 niobium Nb 51 41 vanadium V 23 relative atomic mass – plutonium Pu 150 94 samarium Sm 62 – hassium Hs 108 190 osmium Os 76 101 ruthenium Ru 56 44 iron Fe 26 1 27 28 Co 29 30 Ni Ds 110 195 platinum Pt 78 106 palladium Pd 59 46 nickel Cu Rg 111 197 gold Au 79 108 silver Ag 64 47 copper Cn 112 201 mercury Hg 80 112 cadmium Cd 65 48 zinc Zn – americium Am 152 95 europium Eu 63 – – curium Cm 157 96 gadolinium Gd 64 – – berkelium Bk 159 97 terbium Tb 65 – – californium Cf 163 98 dysprosium Dy 66 – meitnerium darmstadtium roentgenium copernicium Mt 192 109 iridium Ir 77 103 rhodium Rh 59 45 cobalt The volume of one mole of any gas is 24 dm3 at room temperature and pressure (r.t.p.) actinoids lanthanoids 88 85 Y Sr strontium Rb rubidium 45 39 40 38 39 37 Sc scandium Ca calcium K 24 20 23 19 potassium 21 Mg magnesium Na sodium 9 12 7 11 B name atomic symbol Be beryllium Li lithium 7 8 9 VII 2 VIII – einsteinium Es 165 99 holmium Ho 67 204 thallium Tl 115 81 indium In 70 49 gallium Ga 27 31 aluminium Al 11 13 boron C – fermium Fm 167 100 erbium Er 68 – flerovium Fl 114 207 lead Pb 82 119 tin Sn 73 50 germanium Ge 28 32 silicon Si 12 14 carbon N – mendelevium Md 169 101 thulium Tm 69 209 bismuth Bi 83 122 antimony Sb 75 51 arsenic As 31 33 phosphorus P 14 15 nitrogen O – nobelium No 173 102 ytterbium Yb 70 – livermorium Lv 116 – polonium Po 84 128 tellurium Te 79 52 selenium Se 32 34 sulfur S 16 16 oxygen F – lawrencium Lr 175 103 lutetium Lu 71 – astatine At 127 85 iodine I 80 53 bromine Br 35.5 35 chlorine Cl 19 17 fluorine – radon Rn 86 131 xenon Xe 84 54 krypton Kr 40 36 argon Ar 20 18 neon Ne 4 10 He 6 VI helium 5 V H atomic number IV hydrogen 4 III 3 1 Group II I Key 7.2 The Periodic Table of Elements Appendix 125 Data Booklet
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